I'd probably suggest the Droid if you go to Verizon (it's popular so it's like every app is built for the droid), or your choice of Android handset on any provider. Can't go wrong. I was nervous making the leap from WinMo to Android but my fears have all been squelched.
My next phone (unless the iphone gets a significant overhaul this year) will be a nexus one or a nokia n900.
I've had an iphone for 20 months now and have blown through 5 of them (about to be 6). Only once was my fault due to a drop.
If Apple was named Microsoft, there would be rioting in the streets but since it's apple they get some kind of free pass at making a great mobile device but a shitty phone.
I'm done with blackberry too and their fees for enterprise data. I've got users spending 45 bucks a month for enterprise data (BES server contectivity to outlook/exchange requires this package and gives them the same as a 30 dollar iphone plan). I have one guy spending more on data than his voice service.