I have the Diamond and I never had the Pro.
4gb is more than enough for me.
When I first saw the Diamond at the Sprint store, I really liked the style and the fact that it fit in my front jeans pocket so nicely.
Really compact device.
After some registry tweaks, I have it running really nicely.
A big difference was the current stock ROM which became available in April.
It is an unbelievable difference from the original stock ROM that the Diamond came with.
There are issues with screen separation but Sprint has replaced my Diamond without issue covered under the HTC 1 year warranty.
I have TEP also.
I always carry a spare OEM battery just in case I run outta juice.
Was a big issue with the original ROM but not with the current one.
I changed the battery polling registry which makes a big difference regarding battery drainage also.
Most of the Custom ROMS incorporate that tweak anyway.
The size and compactness is a big factor for me.
And there you have my 5 cents