I had been very hesitant to root my D2, but after some reading I used the one click method I found on XDA and it worked flawlessly!
Now I'm back to rooted bliss! I've got Root, Rom Manager (and premium), Bootstrap and am about to try a new rom!
Go down to the second post and the instructions will easily walk you through root with ONE click! I did this and can tell you it works flawlessly!
Easier 1-2-3 Droid 2 Root for Windows and Linux (and soon Mac) - xda-developers