There have been several reports of iTunes accounts being compromised and unauthorized App purchases showing up on credit card bills, I’ve never noticed that. However, it still struck me as odd that each time the card was compromised it was the card associated with iTunes. I accept it may be completely coincidental, but at this point, I felt like I had to do something.

My bank offers a service called “ShopSafe” but other banks offer similar services under different names. This service allows you to create a virtual credit card number associated with your account with a specific credit limit for use with one merchant. You can set time limits and credit limits. In my case, I created a virtual card for use only on the iTunes store (which also works with App purchases from the Mac App Store as they bill from the same place) that expires in 12 months with a $150 spending limit. If I end up buying more than $150 worth of Apps, Music or Movies in a year I can adjust the limit (or, perhaps better, adjust my spending habits!) I can keep track of usage on my bank’s website and the charges show up on my regular statement just like any other charge.

If a hacker gets ahold of my iTunes account, they’re limited to $150 of damage. If this number is compromised, any charge to a merchant other than the iTunes store will be declined. I have no idea if this will do anything, but it does give me extra peace of mind.

If this is something that concerns you, you may want to check and see if your bank or credit card provider offers a similar service. I’m going to consider setting up ShopSafe limits for other merchants like Amazon or other frequently used services.

I packed up a large storage tub full of spare cables and old software and took it off to my local Mac Users Group with a sign that read: “Free to Good Home.” I came back with an empty tub. I’ve also donated boxes of books to our local Friends of the Library and taken several more boxes of household items to charitable organizations.

However, there were a few tech and larger items of value that I wanted to sell and try to recoup some of the investment, especially considering I had some significant moving expenses coming up. I despise eBay. Maybe selling an item here or there is okay, but I can’t stand how eBay takes a cut every step of the way. Listing fee, final value fee, PayPal commission, it just keeps going on and on. For tech related items that are still sold,  I much prefer selling on the Amazon Marketplace. Amazon takes a cut too, but one cut at the end, and they tell you up front exactly how much they’ll take at the time you list your item for sale.

I could go on for several paragraphs explaining how the Amazon Marketplace sales process works, but my friends over at CNET recently published a video detailing the process (direct link – also embedded below) that’s worth checking out. The one new addition that CNET didn’t cover is that now Amazon also integrates with Stamps.com and allows you to print shipping labels and charge posting directly to your Amazon account which effectively deducts it from your profits. I really like this feature, especially because I have access to a postal scale at work and can easily weigh and package my shipments.

Another avenue I’ve used for selling larger items that are impractical to ship is Craigslist. You have to be careful on Craigslist because there are scammers and you are meeting people face-to-face to conduct business and sometimes inviting them into your home. So be careful. I found the Craigslist Mobile iPhone App has helped greatly in my sales process. I can take photos with the iPhone camera, write a brief description and post, all directly from my iPhone.  Best yet, it’s free.

These services have helped me clean house, hopefully they’ll help some of you too.

Here’s my latest (mis)adventure purchasing AppleCare. Thankfully, the story has a happy ending, but it almost cost me.

I purchased a refurbished 24″ Apple Cinema Display last summer. I did not purchase AppleCare from Apple and I generally don’t purchase it until I get closer to my 1 year mark with a product. The reasons I’ve strayed away from immediately purchasing AppleCare with a product are 1) the price when bought direct from Apple and 2) if the product has a non-covered event within the first year of life (i.e. I knock the monitor off my desk and it shatters) then I’m stuck trying to get a pro-rated refund of the AppleCare and have essentially wasted my money.

I decided it was time to purchase AppleCare for my monitor and found several options. Apple charges $99, they were the most expensive. However, I found a reseller through the Amazon Marketplace who sold me the AppleCare for $35. I was a little skeptical, but Amazon has a pretty good consumer protection guarantee so I decided to give it a go and my total price was a little more than $40 after shipping.

The package arrived a week later and sure enough was a retail boxed copy of AppleCare that was sealed. Curiously, inside the package was the Amazon invoice showing my actual purchase price, as well as an invoice from a reseller I had never  heard of with an incorrect date (showed I had purchased the product a couple of months prior) as well as showing the full retail price of the AppleCare. This should have been my first clue. The package arrived the day before I left for a trip so I set it aside for a couple of weeks until I got home and got around to registering it through Apple’s support site.

During the registration process, Apple asked me for a proof of purchase. The instructions weren’t clear and I assumed they wanted a proof of purchase for my monitor to confirm it was still within the one year coverage period. No problem, I sent it off. A couple of days and emails later it became clear they wanted proof of purchase of the AppleCare. Wanting to be honest, I sent them the Amazon.com receipt showing the true purchase date and price. Apple sent me the following email rejecting the AppleCare:

The documentation you sent, however, is not sufficient because it was purchased through an unauthorized reseller. A valid proof of purchase should contain the date of purchase, authorized reseller information, itemized product information, and total price paid.  Contacting the reseller or taking a screenshot of an online invoice may be the best way to obtain a proper receipt.

For further assistance with this issue, please scan and attach your proof of purchase or sales receipt issued by the reseller to an email and send it to…

So I contacted the reseller. They assured me this was no problem and said they would generate a receipt. They provided me with a copy of the same receipt that was inside the package showing an incorrect date and purchase price from a reseller that I never heard of. I asked them for clarification and they explained that this is just “how it works.”  Interesting. So, I sent a reply email to Apple with both receipts and an explanation, making sure that I was clear with Apple that I actually bought the product through Amazon for the lower price. Apple sent back the following response:

Thank you for sending your product’s proof of purchase to Apple.

Apple has re-reviewed your proof of purchase and your request to register your Applecare. Your request was carefully considered. We regret to inform you that your request has been denied.

Your request was denied because the receipt does not reflect the original retail purchase.

Apple does not offer refund for Applecare purchased from a non-Apple authorized reseller such as eBay.  Please contact the reseller for assistance.

Obvious I’m not going to get anywhere with Apple, I contacted the reseller. They tell me just to send my serial number of my product and they’ll register it for me. Mind you, these people have provided no verification of who they are or that they are an Apple authorized reseller. I refuse for fear that if I go through anything other than official Apple channels that I’ll have problems down the line. Several emails later, the reseller agrees to refund my money. So I’m out nothing but my time.

I ultimately ended up buying AppleCare for a discounted price (though higher than my Amazon.com deal) from LA Computer Company. They are an Apple Authorized Reseller and a company I’ve done business with before. This time, I actually spoke to the manager on the phone before my purchase and received his assurances that if there was any problem my money would be refunded. Again, when I went to register the AppleCare I was asked for Proof of Purchase and this time I  fsent AppleCare both my invoice showing the date of purchase of my monitor and my AppleCare and within 12 hours I received a confirmation from Apple that my AppleCare was active.

If you’re looking to save a few bucks on AppleCare, by far the best legitimate deal is to purchase direct from Apple if you qualify for a discount through their Education Sales Program or through some other purchase program. If not, here are a few tips I would suggest to make sure you don’t get burned:

• Consider only buying from an Apple Authorized Reseller.
• Leave yourself a cushion before your 1 year AppleCare expires incase you have problems.
• Once you receive your AppleCare, immediately register it with Apple so you have ample time to dispute the transaction or request a refund if there are any problems.
• Pay with some kind of method or through a service that allows you to dispute the transaction if you have problems.
• Keep your proof or purchase and AppleCare documentation for the life of your covered product.
• If something feels suspect, it probably is.

Black Friday is one of the few days that Apple will put products on sale. You can find discounts around 5 – 10% on Macs, iPod, software and accessories. If you’re looking to buy from Apple direct and are not otherwise eligible for a discount from Apple, Black Friday is typically one of the best days of the year to do it.

In addition to Apple, many Apple Resellers will be offering great deals on Macs and other Apple products. If you’re in the market for a new computer or looking to buy one as a gift, Black Friday can be one of the best days of the year to get a discount, especially if you can find an older model. I’ve had several friends and family members buy Macs on Black Friday and have gotten killer deals. Check the Mac resellers, specifically MacConnection and MacMall.

Check the deal aggregator sites, they tend to gear up for Black Friday. Two of my favorite sites are DealMac and DealBrothers.  You can also preview the Black Friday ads early (though take their accuracy with a grain of salt) on the Deal News Black Friday site.

Lastly, once you’ve got the best deal you can get, try to sweeten it a little bit more with a coupon. Free shipping, an extra percentage off, every little bit helps. A couple of my favorite sites are RetailMeNot and DealCoupon though there are others.

What are your ways to save money on Apple products?

I favor buying a product when you need it. If you keep waiting for the next greatest thing you’ll never upgrade because you’ll constantly be waiting for something better to be right released. Newsflash: something better will always be released.  That new computer you bought will only be the latest and greatest for so long, get over it.

That being said, if you can, avoid buying right before Apple announces an upgrade. Apple user to have fairly predictable upgrade cycles with Macworld in January and WWDC in June but now they call their own press conferences and things are a little more difficult to predict. MacRumors has a Buyers Guide that can offer some guidance. It gives statistical data on when a product was last refreshed, a summary of the latest rumors and a timeline of past updates. It’s not a sure bet, but it will give some guidance and hopefully allow you to avoid smacking your head when you find out that Apple released an update just two weeks after your purchase.

If Apple releases an update immediately after your purchase, you may have some options. Apple’s pricing policy states that if Apple reduces it’s price on any shipped product within 14 calendar days of shipment you can request a refund or credit of the difference. Apple also has a 14 day return and refund period, however a 10% restocking fee may apply. You can find full details on Apple’s website and should review the policies before your purchase as they may change between the time I’ve written this post and the time of your purchase.

Where To Buy

If you’re looking for the latest and greatest with the most customization options, Apple’s website or an Apple Store is probably the way to go. The Apple Website offers build to order and customization options on just about every machine. Some of these options are available in store, some aren’t.

If you’re going to buy one of the stock configurations of a machine, it’s worth the time and effort to compare prices. There are numerous Apple Authorized Resellers that will offer special deals or bundles that will beat Apple’s offerings.  AppleInsider keeps a pricing guide that is updated regularly. Usually, prices on Apple machines don’t vary much, but special deals may make a difference in your buying decision. You should also consider tax and shipping, some resellers require that you pay it, some don’t. Of course, check your local laws as you may be responsible for the taxes even if it isn’t collected by the retailer.

If you are affiliated with an educational institution, check to see if you qualify for an Apple Education discount. You can save anywhere from $50 – $300 on the purchase of a Mac and accessories. Likewise, if you work in government or for a large business you may also be eligible for discounted pricing direct from Apple.

Refurbished Deals

Besides looking for the best price as mentioned above, there are other ways to find deals. One of my favorite ways to get a significant discount on a Mac is to buy from Apple’s “Special Deals” section of the store. This section typically includes refurbished machines and sometimes new machines that are not the current revision. You can easily save a couple hundred dollars on the purchase of a refurbished machine. Before I make a purchase, I always check the refurb store.

Some people are nervous about buying refurbished Macs, but I prefer it if I can find the machine that I want. Let me explain.  First, you save money and I’m all about saving money. Second, you’re getting a machine that you know has been inspected by a technician and restored to Apple’s stringent standards. On a new assembly line run, only a handful of every couple hundred or thousand machines gets tested for quality control purposes. It’s possible that you get a dud that comes off the line. With a refurb, you’re getting a machine that has already had a little TLC from Apple’s techs. Third, Apple has very high standards. Every refurbished Apple product I have purchased looks and feels new. (It even has that new computer smell!) It may have a plain brown box (that is a little disappointing) but otherwise it’s just like a new Mac. Fourth, refurb products are fully eligible for AppleCare and came with the same warranty as new produces. In other words, Apple stands behind them. Lastly, on occasion, you find a little “surprise” inside a refurb product. A hard drive upgrade, extra RAM, etc. Not often, but sometimes the product you get is on that has been custom configured by the original purchaser, so you get the benefit and end up with a bonus.

Other Deals:

There are other deals to be had on Mac related products and accessories if you know where to look. One of my favorite sites is DealMac because they prescreen their vendors and list only reputable sources. I also suggest that if you’re shopping for AppleCare or MobileMe that you price check as you can regularly find deals on those products through authorized resellers for significant savings, just make sure you’re buying from a legitimate source. Here are a few other promotions you should look into:

• Save $30 on the purchase of MobileMe with the purchase of a new Mac or an iPhone
• Save $30 on the purchase of iWork with the purchase of a new Mac
• Mail in Rebates for qualifying printers
• Free iPod for education purchases during Apple’s “Back to School” promotion (Only during summer months.)

If you’re considering purchasing through Amazon, I would appreciate it if you would use the Amazon link in my sidebar. It costs you nothing, but if you buy a very small portion of the purchase comes back to me. It helps pay the hosting costs. Happy shopping!

Here’s my rationale…

I am on a roughly two and a half year upgrade cycle with my Macs. I’ve been keeping to this schedule for the last 10 years or so and it seems to suit me well. Normally, I tell people that a Mac has a much longer life cycle than a typical PC and will easily last three to five years, perhaps longer. However, I like to be on the newer edge of technology so I stay updated more frequently.

Looking at product cycles, there tends to be major upgrades to machines every two to three years with a series of speed bumps and enhancements in between. Keeping myself on this cycle allows me to take advantage major enhancements to a product line rather than just the occasional processor and hard drive bump. Things don’t always work out this way, but when they do it’s a bonus.

It’s easy to be tempted to upgrade more frequently, especially when new machines are released and yours is no longer the latest and greatest. To help stave off the temptation, I usually try to treat my Mac to a little upgrade about mid-way through my upgrade cycle. Somewhere between a year and 18 months I’ll look at a RAM upgrade or perhaps putting in a larger or faster hard drive. Something inexpensive, usually $200 or less that will give my Mac a little refresh and speed boost to give it that “new Mac feeling” again and get me through the next year or so. This year, I think I may invest in a 500GB “hybrid” hard drive for my MacBook Pro that uses a combination of traditional drive technology and Solid State Storage for faster performance.

When it is time to upgrade, I want to get the best price I can out of my Mac so I can use that to offset the purchase of a new machine. Another reason to keep on a two to three year upgrade cycle is that a two to three year old Mac still has lots of life, and thus good value left in it. It’s also important to me that the buyer have a good experience.  The reality is, stuff happens. For all you know, the Mac that has never given you a bit of trouble dies three days after you sell it to the new owner. This is always a tough situation because it’s really no ones fault (assuming you were honest and didn’t deceive the buyer) but the buyer will undoubtedly feel cheated. For that reason, I always make it a point to sell my Macs when they still have a couple of months left of AppleCare coverage. That way if anything happens, the new buyer is dealing with Apple not with me. AppleCare also adds to the resale value. (I also make it a point to warn any buyer that hard drives are temperamental and can die suddenly and without warning and educate them about the importance of backups.) I try to arrange things so that a Mac has two to three months of AppleCare remaining at a minimum when it is transferred to the new buyer.

To enhance the resale value of my Mac I make sure that it is in pristine condition and keep all the boxes, manuals and original accessories. I will also throw in all the upgrades I’ve made to the machine including the latest Apple software since the newest versions will come with my new Mac. I’ll first try to sell the Mac through my local Apple Users Group so I can deal with someone I know or have a connection to. If I’m able to do that, I’ll throw in as an added bonus some of my time to help the person setup the new Mac if they so desire. Selling the Mac to someone you know or through a network of friends is a much better and safer experience than dealing with Craigslist or eBay. Now I’ve built up a good reputation and I regularly get to visit my 500 MHz Titanium PowerBook and my 1GHz 12” PowerBook at User Group meetings. They’re still in good use and their owners are happy purchasers.

In short, the two and a half year upgrade cycle seems to work well for me. I can stay regularly updated with close to the latest and greatest machine while still getting good resale value out of my old machine. I’m afraid if I upgraded more frequently I’d be loosing more money on the resale and if I lengthened the period I’d potentially run into problems with the machine being out of AppleCare and possibly being behind the technology curve.

My upgrade methodology won’t work well for everyone. If you’re looking to get the most bang for your buck your best bet is to buy your computer and hold on to it for as long as possible. It’s not uncommon for a Mac to have a useful life of five years or beyond, especially if you’re performing fairly casual activities such as web browsing, email, word processing, etc. So do your own research and see what works best for your needs.

As a general rule, I don’t like extended warranties and almost universally refuse to buy them. However, the major exception to that is AppleCare. I always buy AppleCare on my portable Macs and strongly recommend it for the purchase of any notebook or iMac. Notebooks are prone to everyday bumps and jostles that can cause damage to the internal components. Notebooks have a higher failure rate than desktop machines and a repair can cost anywhere from a couple hundred dollars to practically the price of a new machine.

I recommend AppleCare on the iMac because the compact form factor and large display is another source of problems. The iMac is very difficult for even the most technically advanced consumer to repair themselves, and the cost of even a minor repair will be very expensive.

On the Mac Pro and the Mac Mini I’m a little more neutral on the idea of AppleCare. Every machine comes with a 1 year standard warranty and my experience is if something was going to go wrong it will likely so in the first year. These machines are also less prone to everyday wear and tear simply because they’re stationary. On a Mac Pro or high end Mac Mini, AppleCare may make more sense because of the cost of replacement. It’s also worth noting that if you buy a display with your MacPro or Mac Mini it will also be covered by AppleCare, so you get a little extra bang for the buck.

I do not recommend AppleCare on iPods, AppleTVs, iPhones or iPads. On these devices AppleCare only extends the warranty of the device from 1 year to two years, so you’re paying for not a lot of extra coverage. These devices are also most prone to accidental damage, loss or theft, which are not covered by AppleCare.

In Summary:

Notebooks and iMacs – Strongly Recommend AppleCare

Mac Pros and Mac Minis – Neutral/Recommend (strongly recommend if buying with a covered display)

Portable Devices – Discourage AppleCare Purchase

David Sparks and I spoke at length about the topic of AppleCare on Mac Power Users Episode 14, Buying and Selling Macs. If you’re interested in this topic, I’d recommend you take a listen.

Insurance vs. AppleCare

Typically, insurance and AppleCare cover different things. AppleCare only covers manufacturer defects. It does not cover loss, theft, accidental damage, etc. By constrast, insurance typically doesn’t cover manufacturer defects but may cover loss, theft and accidental damage. If you want to be fully covered, you may need to purchase both AppleCare and insurance. (SquareTrade is the exception in that it provides some extended warranty benefits.)

Insurance Options:

There are a couple of different insurance options. These options will vary depending on your area and your situation. I can only speak from personal experience and quotes that I have received. So the information I provide below is based on my quotes, your coverage options and prices may vary.

Local Agent:

I consulted my local State Farm agent to find coverage for my notebook, this is my preferred method of insuring mobile devices. I’ve found the costs to be the most competitive and I’m much more comfortable dealing with someone I have a personal relationship with and can deal with locally. I have auto and home insurance through State Farm so I called them up to discuss the possibility of adding coverage for some of my mobile devices and this is what I learned:

Homeowners/Renters insurance will only cover technology under specific circumstances, and typically there’s a deductable. There is also the concern of the adverse impact filing a claim will have and the risk your insurance company will drop you or raise your rates. You should contact your insurance agent to determine what coverage you have under your policy, or ask about the possibility of adding a rider to cover your mobile devices. However, I found that having a separate policy made the most sense for me.

My agent recommended a Marine Policy for my MacBook Pro. It would be a policy separate from my homeowners and auto insurance so that if I had to file a claim on that policy, I wouldn’t run the rick of my homeowners or auto insurance rates going up or being canceled. I also had the advantage of the policy having no deductable and would cover my MacBook Pro for replacement value. Unfortunately, the agent could not sell me coverage on my iPhone or iPad. He told me they use to offer phone insurance, but had to stop. My $0 deductable policy for my MacBook Pro costs me around $35 a year and covers theft, loss and accidental damage. For me, the peace of mind is worth the minimal cost.

You can probably get the best deals from a company you already do business with. But if you don’t get the answer you want form your local agent, try the agent for another company. They all have different policies and different options. Insurance varies by state. For example, I know some of my podcasting friends in California can’t get this type of coverage from their State Farm agent, so availability varies.

Technology Specific Insurance Companies

There are a couple of insurance companies out there that specialize in insurance for mobile devices. Safeware and SquareTrade are the most popular options, although there may be others. David Sparks turned me on to this idea and has policies on his mobile devices with Safeware and SquareTrade however he’s never had to file a claim so can’t speak to that process.

Both these companies offer insurance for notebooks, iPhones and iPads. Safeware offers protection from theft, accidental damage, power surge, and theft.  SquareTrade takes a slightly different approach and offers a more traditional extended warranty plan with the option to add accidental damage protection for another premium. (Loss or theft protection typically isn’t available from SquareTrade.) Because each of these companies offer different solutions depending on the product you want to cover, I suggest you look at both options to compare the features.

I have no personal experience with either of these companies. Please perform your due diligence and investigate their terms and reputation.

Insurance from the Retailer

Insurance may also be available from your carrier or retailer. Most phone companies and retail stores offer some kind of insurance or extended warranty policy. Make sure you investigate these options and their cost. Be sure to look out for unexpected deductibles and monthly fees. BestBuy has an extended warranty program and AT&T is supposedly getting into the iPhone insurance business soon.

Do Warranties and Insurance Make Sense?

This is a highly debatable issue. As a general rule, I avoid extended warranties. My philosophy is that devices will typically fail within the normal warranty coverage due to some kind of design or manufacturing defect or they’ll last until they wear themselves out, typically after a warranty period has ended. You can spend a lot of money on additional warranties and insurance that you never use and wish you had that money in your pocket to buy other things.

If you’re particularly accident prone, or the device is going to be used by someone who is accident prone (teenage boys for example) then insurance may make more sense. Just keep in mind, it is insurance and if you file a claim or two, you’ll probably be dropped or non-renewed.

Insurance or extended warranties may make more sense if the cost of replacing the device would be a significant hardship or impossible due to your financial circumstances. However, you also must ask yourself, if you don’t have appropriate savings to cover an unexpected device replacement, should you really be spending your money on that device in the first place?

There is also the peace of mind factor that comes into play. If you’re so paranoid that you’re going to loose or break your laptop that you never take it out of the house, why did you even bother to buy a laptop? In this case, your fear is depriving you of using the device to the full potential. If this is a serious concern, you may want to consider buying the insurance and living your life.

Other Options:

Explore what type of insurance you may already have on your devices. Does your existing insurance cover your devices? If so, under what circumstances?  Do you have any alternative sources of coverage? Some credit cards may offer extended warranties or replacement protections on some purchase. Make sure you explore these possibilities as well. If you use your device for business, is it possibly covered under your employers insurance or will they pay for repairs or replacements? There are all kinds of special circumstances out there, make sure you explore your options fully.

Read the Fine Print:

Make sure you know what you’re getting yourself into before you buy anything. What’s covered and what’s not? What’s the deductable? What’s the claims process like? Can you immediately go out and replace the device or is their some kind of waiting or investigation period?  What are the remedies if you’re not satisfied with your service? Make sure you understand the terms and conditions of your contract before you hand over your cash.

Always Have a Plan B:

Insurance coverage may not be perfect. In many cases there is a period of time when you’re without your device while the claim is investigated or the item is off for repair. In the case of a phone or computer, that can be a big deal. What’s your contingency plan?

Be Smart

Insurance only covers the replacement of the device: not the data on the device or the potential consequences of lost data. As always, make sure you have appropriate backups and security methods so that if your device is destroyed, lost or stolen, you don’t also have to deal with the possible repercussions of data theft or reproducing your work.