My vote goes to the Milestone (Droid).
I don't want to rely solely on a virtual keyboard and despite the Milestone's keyboard not being instantly perfect, it does become better and more familiar with use. When I first had a BB it took me forever to type a short e-mail, whereas now I'm fast and don't need to think about it.
Google as a phone provider is a bit of an unknown quantity. Throwing money at something and having the perceived limitless resources available are not always a recipe for success. You could make a comparison to a number of football teams (soccer for those with other ideas!) who have millions invested, buy THE players, but yet don't pull off the results that logic would say the combination would provide.
Motorola, with its telecoms pedigree, is telecoms focused, rather than thinking "we've got all this cash, what can we diversify into now"? I would hope that with this market development/challenge to their market, that they will work overtime to ensure that everything they manufacture, provide and update is market leading. Can they afford to do otherwise?
This was an interesting reply on another forum to a question I asked about whether the Milestone is already out of date, especially with the Nexus and forthcoming X10:
"I think the simple answer to your question is that a Snapdragon processor in a handset will, by itself, not make the Milestone feel like yesterday's technology.
The OMAP 3 in the Milestone (also used in the Satio and the N900) is pretty much as capable as the Snapdragon.
I think the Milestone will feel a bit yesterday compared to some upcoming Android sets but more for software reasons than hardware reasons."
I'd hope that the software disadvantage is only temporary.
Long answer, but the Milestone, as un-sexy compared to the HD2 as it might be (and I'm easily sold on esthetics!), is most definitely the one for me for 2010.