You make a great point for ME to root. But, if my guys root and have issues, I pay if they have any problems. I need to be more cautious with them. If all goes well with me...then you know...trickle down.
Of course, you always run the risk of bricking a phone when you are doing an update (even with OTA updates), but I wouldn't worry too much. You can normally flash back to stock if you need warranty work.
Below is a link to the guide that I followed when rooting my phone.
Root your DROID and install the Bugless Beast ROM - SmartPhoneADDICTED
The guide uses Bugless Beast (based on 2.1) and I have found all of the 2.1 Droid ROMs to be quite unstable. So, I switched to Bugless Beauty (based on 2.0.1) which is actually more stable than the stock 2.0.1 ROM. Once the official 2.1 OTA comes out, all of this will change though, since the cooks will have a good basis for their patches.