My DROID has gone from Stock to Root to near dead to back to Stock (via flashing the device using RSDLite).
I flashed 2.0 on it, then manually updated to 2.0.1, then 2.1. I had manually update because the OTA updates weren't working.
I'm hoping when 2.2 hits next week my phone will pick up the OTA update. Any reason why it wouldn't? I did have root access but it's since been flashed back to all stock non-rooted. I'd assume it'll work but I just wanted to get a few more opinions...