Wow, they are really committed to this pretty convoluted update path. The majority of customers will go along with this upgrade path, but can you imagine what it will be like walking through helping customer's back up their Macs (prudent before any software update), helping them install Snow Leopard, then assisting them in updating to the latest SL version, then helping them log into the Mac App Store to download Lion? It may be hard to believe given the proficiency among users here in Mac products, but for some customers, just figuring out how to sign into the Mac App Store will be a 30-minute phone call to Apple: "My Apple ID, is that what I use on the Google? Or is that my 3G password?" When MobileMe shuts down, there is going to be a "bag of hurt," including for the people taking phone calls related to supporting these customers.
I can imagine the calls right now,
Customer: "I have to back-up my computer and install this Snow Leopard just so that I can keep my e-mail I've been paying a $100 a year for for the last 10 years?!?!"
Advisor: "Actually after backing up your computer, installing Snow Leopard, you'll need to buy Lion, and after installing that you can keep your e-mail service."
Customer: (supernova exploding)
Personally, I finally gave in and updated to Lion, but before I did, I frequently contacted Apple to verify my MobileMe (and later iCloud) e-mail would continue functioning with Snow Leopard. I was given cagey answers, but the general consensus was that it would not. I don't believe that is the case, but nonetheless, how difficult would it have been for Apple to update Snow Leopard to work with the iCloud e-mail service and the calendar, contact, syncing, etc? After all, Apple is supporting Windows Vista! Windows Vista is the operating system Apple spent hundreds of millions of dollars lambasting on television. If it's capable of using iCloud, why not Snow Leopard, the OS which Apple advertised as being so much better than Vista?
Apple has historically been pretty bad with maintaining any sort of online services for any length of time (the exception being the iTunes Store). They deprecate services before there's even a fully functional alternative. I have accounts with Tripod from the late 90s and they are still storing all of my files without interruption. I have a Gmail account as a back-up e-mail, and I don't have to worry about losing e-mail if I don't switch to a renamed service or if I am using a slightly older operating system.
Apple should care a little more about polishing Lion rather than trying to get everyone onto it.
With Apple everything is supposed to "just work." But honestly, the upgrade path to iCloud would be more simple if Apple sent all these users a copy of Windows Vista and had them install it via Boot Camp. It would probably require about the same number of steps!
