I would say get used to the phone for at least a week before rooting, just so you understand the phone well. I rooted mine shortly after I bought it and it was a little confusing at first (back in January, pre-2.1) but it might be easier now.
this should help you decide. go check out the droid hacking section as well, theres a lot of great info in there for you to look through. probably even help you decide on what you are going to do.
im going to lock this because it's in the wrong section as well as it has been discussed multiple times which you can look at in the hacking section.
i have a rooted droid so i mean if you have any questions feel free to PM me. not sure if ill be available at that exact moment but ill reply as soon as i can.