I wouldn't look to a TP2 to handle drops onto concrete like your old iPAQ. You'd probably be picking up a now two-piece phone. At least if it is anything like my old HTC PPC6800 (Mogul/Titan 100).
I tend to use my phone a lot, but at the same time baby it, so I don't have quite the record that you display. I lost one Motorola Q in a blizzard when it came out of the factory holster, and years ago, I lost an old Qualcomm phone when I left it on my table as I went to pay my bill in a restaurant. Every other phone has lasted, in decent shape, until I replaced them out of boredom.
The Windows Mobile Platform is decent enough, but after running it since Windows CE 2 (on an old Phillips PDA), I was thoroughly bored, and neither WinMo 6.1 (which I was running on my HTC through a cooked ROM) nor 6.5 were going to be that much different. That is how I ended up with my current Curve. Well, the QWERTY keypad had a bunch to do with it as well.
I have been extremely pleased with my BlackBerry so far. The interface just makes sense. I find that since I've gone to it I'm using the Internet more than I ever did on either my HTC or my Q.
Good luck whichever way you go!
Red BB Curve 8330m
v.4.5.138 (Platform 184.108.40.206)