I was afraid to root and rom my Droid for a long time, mostly because I didn't know exactly what to expect. If you're the kind of person that likes to know what going on when you root and rom use this guide:
http://www.droidforums.net/forum/ha...ng-only-sprecovery-terminal-emulator-zip.html
It takes you step by step and explains
everything. So, when you're done, you actually know what you've done!
The DroidMod program is good too. It does all the dirty work for you. I didn't like that option too much because I'm a beginer and I like to know what I'm doing so if something goes wrong I know how to fix it. After I'm well versed I probably will switch to a more automated option like DroidMod.