I had two WinMo phones before my Hero (PPC6700 and Touch). Out of the box, few phones are more completely dysfunctional than a phone running Windows Mobile. HOWEVER, if you spend a few days installing the right thirdparty apps & extensions, and tweak it heavily, they can be decent.
Like Android, most phones running Windows Mobile are about 2/3 as fast as you're likely to want them to be.
The first app you install should... no, wait... MUST... be "S2U2". A Windows Mobile phone without S2U2 and touchscreen that can activate in your pocket is a disaster waiting to happen. If Microsoft had a picogram of common sense, they'd hunt down the guy who wrote S2U2 and make him the lead developer for WM7.
That's how utterly essential S2U2 is.
Another worthwhile app even though it's not free is "Winterface" by Vito Tech. If it doesn't come for free with your phone, spend the thirty bucks and buy Opera Mobile, too. It blows Internet Explorer away so badly, it's not even funny.
It might sound funky, but if it has a resistive screen, discreetly shape the nail on your index finger into a flattened, blunted triangle. It doesn't have to be really obvious or anything, just a gentle bit of a tip on the end. Then you can forget the stylus for 98% of your tasks, and just use your fingernail. I did it for years, going all the way back to my Samsung SPH-i300 in 2001. Speaking of styli, though... spend the ~$20 or so and buy a 3-pack of Seidio telescoping styli with pens inside. Even if you don't need them as styli, it's always handy to have a pen available to sign checks with and stuff.
Finally, check out xda-developers.com. If you get lucky, you might be able to have your cake & eat it too... a phone that comes with Windows Mobile that can be trivially booted into Android using HaRet. No commitment required... it literally boots Android from a zipfile on your microSD card without affecting a single byte of your phone's native flash. I don't think the TouchHD2 has a viable Android port yet... but I put the odds at at least 50% that it will by the end of the year
That said, there's one scenario almost every WinMo user comes to hate that seems to happen once every few weeks:
(ring)
[press green button to answer]
(ring)
[press green button again]
(ring)
[press green button REALLY HARD, once or twice.]
(ri--- silence)
[violent profanity that can't be printed in a family-friendly forum]
(voicemail indicator)
[blood pressure spikes to potentially lethal levels... phone comes within ~40 milliseconds of being smashed onto the floor in rage...]
Fortunately, that hasn't happened with my Hero. Yet.