Jones has truth.
Apple is the more user-friendly and intuitive OS, tons of apps, and a beautiful phone to boot. Winmo is catching up in the aesthetics dept arguably, with some really nice phones, but the underlying software is in need of serious updating. Fuck 6.5.
My Mogul was hacked to bejeezus, running one of DCD's roms, and using SpB and a couple plugins to increase finger usability (the OS was built around a stylus and you can tell), but no matter what hacks I did, or whatever pretty skins, or launchers I used, the clicks still led to the same disjointed, utilitarian apps(though still highly usable). Tinkering to see what you could get was a lot of fun in Winmo though.
Now if you like linux I'd get a Pre. I have a functional terminal screen built into my phone. Fuck yes.