The sync libraries are totally separate

Well, that is one piece of the puzzle then. I might consider looking into the iTunes plugin angle just out of personal curiousity (I don't see it as the best solution for my needs), but I can't find any source code for an existing iTunes Device Plugin. I have the iTunes plugin SDK, but it only has sample source code for a display plugin which is totally different. Anybody know of an existing iTunes device plugin that is open source?

-Mike