IMHO, Id do it. If you do then the droid might be the best choice since you wont go through 'keyboard withdrawal' Android has matured to a very stable and able contender and IMO its like a faster, more finger friendly version of winmo. I have not find anything that winmo did that Android did not, its just as customizeable, hackable, tons and tons of apps, faster, smoother, etc.

Im not taking anything away from winmo but 6.5 is behind the times so there are way better alternatives till WM7 hits.

my money is on WebOS though....