I've used Windows Mobile PDAs in the past so I'm familiar with the platform. Windows Mobile 6.x is straight-up outdated, but knowing Microsoft they'll redeem themselves with Windows Mobile 7 (have they ever lagged this far behind for more than one operating system generation? no.), but that won't be out until middle/late next year. Furthermore, writing applications for Android looks to be really simple (like two semester-long computer science courses, and the SDK is a plugin to Eclipse JDE), and that's something that I already have a list of applications to custom-build.
I guess I'll go with the Droid and just deal with the scrunched keyboard.
If a hard keyboard is required with Android 2, and hell, Verizon in general, you might be waiting awhile.
There is a Snapdragon-based Android phone on the horizon (same hardware as the HTC HD2, spyshots show it might look a little different, not as sexy as the proper HD2 with WinMo, as far as the physical build). I reckon it would be Android 2, but release date unknown although rumored to be late December or sometime in the first quarter of next year. But, no keyboard, like the HD2.
I've made do with the Droid's keyboard, it serves its purpose.
My Samsung Omnia had no keyboard, so just having a keyboard is quite a bit better. And the software keyboard (well, using Better Keyboard) is worlds better than any keyboard replacement I used in WinMo. So I'm far more capable already, plus, this phone spanks the Omnia in every way possible. It's not WinMo, it's stable, and memory management is something I never have to worry about (WinMo sucks ass at memory management).
As for the WinMo versus Android argument, I am finding myself preferring Android more and more. Like I said, I had the Omnia and spent, iirc, 8 months with the phone. I modded it because the basic WinMo6.1 OS was junk for touch (Omnia had a Resistive screen too, bah. i put the stylus somewhere, no sure where). Flashed modded firmware before Verizon officially released the GPS unlock, and kept playing around with different ROMs and UI applications.
It started getting a lot better in the summer and fall, when WinMo 6.5 ROMs were starting to mature. Had the new style (that Microsoft has yet to release, is coming soon) with the touch-optimized notification bar and main buttons, including Start, at the bottom and more touch friendly. Worlds better, and the UI everywhere had improved quite a bit. Even the ancient-looking Alarm screen received an update that made it far more friendly.
But customization, and getting an assortment of apps, was a tiresome process.
The open nature of the Android platform is already allowing a huge stream of apps in the Market. Sure, some are junk, as people with little experience coding release something they don't intend to spend a lot of time on... but you also get the developers who release a quality product, or spend a lot of time releasing updates to make sure it works. And the community is great, people work together to accomplish development goals. It didn't take long for an LED Flashlight app to be released for the Droid, and quite a few people were working together on a few different boards to try and get something working.
Not saying you don't have that with WinMo, because on the contrary, xda-developers.com and modaco.com had thriving communities built around Winmo customization. But I am enjoying my Droid far more than I ever dreamed with my Omnia, it was just little issues that kept it from being the phone I needed it to be. The Droid is super stable, very reliable so that I don't need to worry about it not being there for me based on what I need at the time, and quite a few apps that just craft this phone into something I never thought possible.