I thought there might be an easy way to restart the winamp session
No, as you have now seen, once Xlobby looses default control, you can't get it back unless you do a restart. Now there are other ways of getting control of a rogue Winamp, and that is by sending window messages or command line commands to it. Though you still have lost feedback, and playlist control. Chances are the developer of Freebox would be reluctant to take this sort of control out of his software. He wants his software to primarily control the computers sound output. Too bad as if he left other players alone, and you had multiple soundcards, then you could assign Freebox to the primary sound card, and then assign winamp to the secondary soundcard.
But in the end, if Xlobby can do pretty much everything that Freebox can do, then why use Freebox?
Is there a skin with a more traditional looking jukebox screen I could put into my colby skin?
There's a skin called Sid's Jukebox which is pretty cool. I don't know how simple it would be to integrate into another skin, but standalone, it is a really great skin. You can download it from Sharp's google pages (find a post of Sharp_1, his google pages are linked in his signature), as the link on the Xlobby/Download/Skin page didn't work for me.
ps. 1 more problem (last one I promise)... when i select an album the overlay will pop up with the art and the tracks. Some of the albums show a blank spot where the track should be. The blank can still be clicked and the proper song loaded though.
Example...
1. Song title one
2. Song title two
4. Song title Four
5. Song title five
This sounds as though you have a tagging issue. Check your tags using a tag editor. I like Tag n' Rename and the Godfather. There are plenty of them to choose. I don't usually muck too much with v1 tags...more like I clear them and just mess with the later tagging scheme.
Hope that helps.