I'm staying with Verizon and so far, the Droid is the king with them. There is a Devour coming in March but it's the Droid's little brother, as I have read somewhere so I will stay with Droid for now.
What he said.yes you will have to back to stock 2.0.1 before applying official update. Nothing stops you from trying on modified roms such as ported 2.1, but there's an extremely high chance it will fail (especially on 2.1). If you are already rooted I would just stay the course. When the official update comes out you know all the devs will get their hands on it, maybe even before most people, and they will have it out with root in no time.