I've had a pocket PC in some form for at least 7 years. I was ready to walk up to the samsung people and force them to choke on my latest windows mobile phone, the sch-i730. I hate it so much. Every time I see it, I want to vomit.
Got out of my contract thanks to verizon's text message rate increases and looked at phones over the weekend. Though there aren't as many apps for it and the virtual keyboard is cludgy, I still couldn't resist the iphone. Basic tasks are so much easier with it. My experience with the samsung taught me that I should aim for a phone that works best for things I would use the most. I fell for the trap of windows CE software downloads one time too many.
I recently got a zune for $80 and over time am kind of sick of it too. It's a less vicious hate because the device itself is pretty decent. The zune software, however, is so much worse than iTunes it makes me consider naming my first born iTunes just to spite Zune. So part of the decision involved getting back to the ipod platform.
Definitely happy with my purchase. In my area, there's no 3G for GSM services at the moment and there won't be for a while.