Looks like a dev over at XDA-Devs (where else?) has managed to root the Motorola Droid 2. As this is the device's first root and it was just released, it's not surprising that the method is still dependant on manually typing a number of commands. The process requires adb and Motorola drivers to be installed, and involves pushing and executing the root file with ADB. While it doesn't look overly complex, it's probably not something suitable for more novice rooters.

Setup:
- Install adb (here) and Motorola drivers (here)
- Download attached archive
- Extract to a directory, I used c:\Droid2Root
- Make sure you have USB degugging enabled
- Change connection to PC Mode

Process:
- Open command prompt
- cd c:/wherever-your-sdk-tools-folder-is
- adb devices (to verify the connection)
- cd c:/Droid2Root
- adb push rageagainstthecage-arm5.bin /data/local/tmp/rageagainstthecage-arm5.bin
- adb shell
- cd data/local/tmp
- chmod 0755 rageagainstthecage-arm5.bin
- ./rageagainstthecage-arm5.bin

- let the process run until it returns you to c:/Droid2Root
- cd c:/wherever-your-sdk-tools-folder-is
- adb devices (to verify the connection)
- adb shell (you should now have a # prompt)
- exit

- cd c:/Droid2Root
- adb push Superuser.apk /system/app/Superuser.apk
- adb push su /system/bin/su
- adb push busybox /system/bin/busybox
- adb shell
- chmod 4755 /system/bin/su
- chmod 4755 /system/bin/busybox
- exit

I'm sure there are certain steps that could be streamlined or eliminated, so please feel free to make a suggestion and I'll edit the post.