First things first: install Android Mate and Astro. Back-up all apps in BOTH programs. They are free, if you want to back-up everything exactly, then spring for Titanium backup, but more than likely you'll be changing stuff around with new options for Home apps. Read more on these links and do some research. The instructions are step-by-step and fairly straight forward, but the assumption is you've done some reading and educated yourself. The best docs still fail to make it perfectly clear for the clueless (speaking from experience).
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Easier instructions - will give you Froyo and believe leaves you rooted, so very easy to swap out roms after (though you probably would need to nandroid restore to go back to a 2.1 rom)
http://www.mydroidworld.com/forums/motorola-droid/2513-non-rooted-users-guide-get-froyo.html
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OK, to root from 2.1, try this: (yes, disclaimer, YOU "WILL" VOID WARRANTY AND COULD RUIN YOUR PHONE....YOU'VE BEEN WARNED).
http://forum.droidmod.org/index.php?PHPSESSID=55060ace771d02bf93a2ce3d3c8651d1&/topic,1004.0.html
Then, just my personal preference, install BuglessBeast v1.1 (34,000+ downloads = ridiculous)
http://www.droidforums.net/forum/bugless/47544-rom-bugless-beast-v1-1-a.html
Some issues you may have with your phone after:
1) dial *228 option #2 to update roaming
2) dial *22899 to re-aquire towers
3) if you haven't done so....Dial ##7764726. This is a "Secret" menu (not so secret). It wont dial anything, but instead its going to ask you for a password. Type "000000" (6- 0's) scroll down to "04 Vocode" -> then select "EVRC-B". go back to home screen then phone will reboot
4) update baseband (last resort, you may not need to do this - I haven't, yet, and it requires reactivating your phone *228 option #1) - different baseband for 2.2 and probably a good idea to update this.
http://www.droidforums.net/forum/woodyman/38607-update-baseband.html#post412535
I recommend playing with BuglessBeast1.1 before going to the 2.2 rom, which has some kinks that will probably be cleaned up over the next 2-4 days. With BuglessBeast, you can re-install all your apps easily with a batch install from Astro. That doesn't work with the Froyo rom and you will have to do one-at-a-time from Android Mate.
http://www.droidforums.net/forum/bugless/47544-rom-bugless-beast-v1-1-a.html
After a few days, you can go to 2.2. If anyone is interested, I'll post a link for a rom to do that (most likely I will go with Bugless when he comes out with it, my guess by no later than end of this week)
I'll try to help, but I haven't rooted from 2.1. Instructions are pretty good if you follow exactly, but there always seems to be something missing that is obvious common sense to only the techies. It took me probably 4 hours to read and understand and successfully root the first time. Once you've installed a rom, it's pretty easy to do a nandroid install or update.zip. I can't support you - I get all my tips and insights from the Droid forums.
I use SPRecovery. Many are using Clockwork now. Those seem to be the two routes to go to ultimately upgrade to Froyo.
You can wait a few weeks and VZW will probably roll out Froyo, but if the bugs in the hacked version are any indication I beleive it will be much longer. VZW doesn't take those sort of customer service risks, which is why 2.1 took so much longer. The process to unroot and go back to stock is not difficult. You may screw up your phone, but it can be fixed. The odds of ruining your phone are virtually nil - actually PERMANENTLY "bricking" the phone seems to be a bit of urban legend, but I don't pretend to be an expert.