Jump right in man, if its for you. Its virtually impossible to brick the phone, just dont do anything foolish like rooting with a drained battery or anything.
I agree with mike... it's not as scary as it looks... once you do it you'll find that there are so many back-up features that will safeguard your Droid... SPRecovery is what you'd use to restore back to what your phone's stae was when you recieved it from VZW, but with SPRecovery installed... then when you go from there to gain root access, and somehow fail, you can boot into recovery and restore to that stock state again...... and then try it again...lol
On top of that, if you download rom manager after you root, it installs it's own recovery software, and anytime you install a different rom it backs up your stuff. On top of that if you use titanium backup too, then your apps and all their information and settings are only a few touches away from reinstalling them all.
Most people talk about using droidmod to do their first root... I would recomend that for a newb... simple, follow instructions, type deal that gets you rooted and gives you a stable easy rom to work with at first... and sprecovery to back out of it if you get over your head... and do it all from the phone.. no need a computer
I did my first root that way sitting on a delayed flight.. only took me 15min and never went back to stock
Further note...I think its harder to think of reasons to NOT root your phone.
1. Warranty (which is easily worked around, so this really isn't an issue)
2. Bricking your phone (which is damn near impossible, and only happens when there are gross oversites.)
3. Your a goody two shoes