I have a Blackberry, and like it. Never been a fan of HTC product (nor has anyone i know), my friend has an instinct and loves it, so that gets my vote
*EDIT* I don't know what OS the HTC runs, but if it runs a variation of Windows mobile, RUN. That is the most unstable OS i've ever encountered...
I currently have the touch pro and love it. It hasn't given me any issues at all since I've had it. Hasn't frozen or crashed a single time like some of the other people above stated. The only phone I had that ever gave me any problem's was the Motorola Q. Only real complaint about the touch pro so far is how bulky it is but that's because I was use to my HTC Touch that I had previous to this.
everytime i get on a widows mobile phone i cringe, that is the most garbage OS ive ever dealt with, im happy i got rid of my treo i had, POS
If you want an unresponsive OS and one you have to restart everyday, go with windows
im also not a fan of the older blackberry stuff, the new storm and bold i do like, i dont have one complaint on my iphone, it just works, and works good