I really want to root and have been researching various mods, methods, etc for awhile now. I've been on the fence for a couple of weeks and am thinking that the link to the DroidMod tutorial in this thread is what's probably going to push me into rooting. My biggest reason for wanting to root is to be able to overclock, as I'm currently happy with the screen and apps that I've got loaded. I'm using Dolphin browser and B&B Gallery so I've got pinch to zoom. I just want the apps to run faster. Im the kind of guy who bought a flash tuner for a new Mustang GT before I had enough miles on the car for it to need it's first oil change. If there was an app or a widget that would let us overclock without rooting that would probably be all I'd need to be perfectly content with my droid.
I know that as soon as I root, 2.1 will come out the next day, OR my phone will malfunction afterwards and I won't be able to get it back to stock in order to get it replaced.
Having said that, the only other thing holding me back is that in my reading on the subject, it appears that no matter what ROM is discussed, it seems there is always some bug that keeps a stock feature from working properly after rooting. Small annoying stuff like the temperature won't display when the phone is in the charging cradle, or the music player doesn't work properly, or issues with google maps (which I use a lot), etc. This is probably the overriding issue that has caused me think twice about it.
I'd be very interested in hearing how this latest DMUpdater is working for first-time rooters.