Users are asking for easy to use, fun devices. Not root.
It's astonishing how many people working in the software industry look at something their customers are clamoring for, say to themselves "I don't want that!" and, because of that, ignore it.
I used to think that this industry was worse off for being largely run by business/marketing people instead of techies, but the older I get, the less strongly I think that.
The point of business is to make things for your customers.
When you make things for yourself, that's a hobby.
Yes, obviously, when you're your own customer and thus your work is also your hobby, that's a wonderful thing: for you and for your work.
So here's a hint for techies: quit taking so much pride in how superior your taste is and how much smarter you are than your customers. That just means it's harder for you to "get into their head" and build what they want in a way they'll want it.
Just works? As in I can get my email to sync more often than 4 times an hour without jailbreaking it?
Just works? As in I can install the grooveshark iPhone app without jailbreaking it?
Just works? As in I can listen to pandora and browse the internet without jailbreaking it?
Just works? As in I can stop the screen from rotation while I'm trying to use the thing in bed without jailbreaking it?
Just works? As in I can use my google voice app without having to resort to the workaround the google coded up?
Just works? As in I can use any song or sound stored on the filesystem as a ringtone, alarm, or alert?
The iPhone might "just work" if you're looking for something that is slightly worse than a netbook for updating your twitter status, but as far as seeing the iPad be anything more than paying $600 for the privilege of then paying to run apps from the iTunes store, well, I don't see it.
Maybe this will change when I get my hands around an iPad, but I very highly doubt it.
Although perhaps I'm just a tad bitter about how absolutely dreadfully horrible the iPhone is at just about everything I've tried to do on it. (Okay, that's a lie, my niece really enjoyed playing with the guitar chord app I downloaded)
Among other things, if you have an Exchange server or an IMAP server that supports IDLE, you get push e-mail automatically, which for me solves that problem in its entirety.
Things like background apps can be done, but the practicality of allowing background apps without draining the battery far too fast is an issue that (to date) they haven't solved effectively. Perhaps in the next generation of apps.
Finally, the rotation - I agree with you wholeheartedly. Rotation inhibitor is the biggest reason why I jailbreak. I hope this will be solved in a future OS release, but who knows.