I have updated SEVERAL android based boxes and have NEVER seen this grey password screen (very strange) one other thing to mention Ray, is that the kind folks at Droid, can actually remote access your box, so if you still have troubles that might be the way to go.
The Wookie by the way is "Ace" it will take a lot of the setting up out of the equation for you but really, you need to make sure that your basic Android OS is functioning correctly first, and of course your actual box!
Good luck mate - let us know how you get on, and if you still find you are getting nowhere and need our help - just yell!
Regards,
Ray(str)