That's right: no flash on the Touch Pro2 nor the Diamond2.
No US carrier offers 2-way video conferencing. AT&T offers one-way (VideoShare), and I would imagine their version of this phone will probably support that. Sorry, no idea when the AT&T version will come out.
When HTC announced the TP2 and Diamond2 they said they would be upgradable to WinMo 6.5, so they should be. No idea about US carrier branded versions though.
The drawback to HTC's ExtUSB connector is that you must use their headset or carry a dongle adapter to use a 3.5mm stereo headset or headphones. Folks really like having a 3.5mm jack on multimedia capable phones.
-------------------- Lisa Gade Editor in Chief, MobileTechReview