I’m not sure Android is the right answer either. They are too fragmented and when they update their OS they break existing apps.
Winmobile 7 looks to not be it either. They are following the apple model of a closed ecosystem where you can’t do the same things as you can with winmob 6.5. Maybe in 2 or 3 years winmobile 7 will be better, but by then the next iPhone will be out and there will be all sorts of andoid phones.
Right now the cell phone market isn’t perfect and there is no magical device that does what I need. I personally like the android and winmob6.5 for MY use, but it’s deinfitely not as friendly for the consumer. Apple has that edge. Winmob 7 looks to take away the power user and go for the dumb user as the iPhone does. This will only leave android in the power user space.
Out of the box iPHone is clearly the easiest to use. Winmob 6.5 after massive tweaks and ROM flashes winmob 6.5 is the best phone. But most users won’t go through all that trouble.
Have you checked WinMo 6.5 on the HTC Touch Pro 2, running SPB Mobile Shell? It's a whole different UI, AMAZINGLY simple and easy, totally 'drag and drop' customizable, and downright sexy.
There's a 14 day free trial of SPB Mobile Shell, and I'd highly recommend trying it. It's what a mobile phone OS should look and operate like. And you still get the most powerful mobile OS out there (WinMo 6.5) to operate on.