For what it's worth, a year into owning my Motorola Droid X, which looked great on paper, I wish I'd gone back into the past and told myself to just get a Nexus S or even a Nexus One. Then, at least, I'd know that any wonky behavior I was experiencing would also likely be suffered by somebody working at Google who'd be more likely to fix it.
As it stands today, with Gingerbread finally on my phone, the phone is oodles better than it was a year ago, but it still crashes and behaves weird at odd times. Under Android 2.2, the problem was that anything touching the GPS would have a non-zero chance of wedging the phone. Now, it's after the phone has been on for a while, it just stops being able to make phone calls and needs to be rebooted. Dollars to doughnuts, this boils down to crappy device drivers.
I pains me to have to wait until next summer before my two year contract with Verizon comes up for renewal. Who knows, maybe by then the whole situation will be better.