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The big question is what will iOS look like. Apple is clever and I can only guess about how tight iOS 5 will be.
Don't mean to pick on you, Bob. You just happened to be in the line of fire.
My central point is simply that the frequent claim that Apple devices are "simple," "elegant," and "just work" is based in part on the restriction of choices that Apple imposes on users. And when that is noted, the answer is frequently that jailbreaking solves that problem. But that answer sacrifices, at least to some extent, a major (if not the primary) benefit cited for Apple devices. Furthermore, it's not even available as a choice for the vast majority of users.
There's nothing wrong with making tinkering with and maintaining a computing device a hobby. I've done it, myself. Rooted my first Android phone and assisted a number of others who managed to descend into the hell of keeping up with new roms, dealing with software incompatibilities, and even wiping their operating systems without understanding what they were doing.
It was fun...for awhile. But as someone who has a household full of computers and smartphones the last thing I need is still another device that requires me to keep track of whether the latest rom release from god knows who is the source of an anomaly I've experienced with my tablet.
Like Palpatine, I'm perfectly willing to put up with the "jail" Apple puts my iPad in. If my iPad were my main computer I'd be more resentful of the restrictions. But there are so many inadequacies in the iPad (both in terms of software restrictions and hardware limitations) for that purpose that jailbreaking wouldn't help.
As it is, my iPad does a great job for media consumption and limited content creation. I don't expect it to handle the avalanche of email I receive every day nor to act as the primary exchange client for corporate communication. I don't want to (or have to) jump through the hoops that would be involved in a handling complex Excel spreadsheets via Office emulators like Documents to Go.
Bottom line in terms of this thread. If you need a computer, get a computer. If you want a tablet, imo, the iPad is currently the best choice, warts and all. If you need a bit more laptop functionality and face budget constraints, the Lenovo ThinkPad Tablet or the ASUS Tablet w/ keyboard are reasonable choices. But don't fool yourself into believing there are no compromises.