I guess in the end, the best hope is that static playlists can be managed from the web interface soon. But barring that, can anyone tell me more about how to make option #3 work?
Actually, things have actually moved along quite a bit in the last month on the static playlist side.
But to make #3 work, just drop your iTunes xml in the root of the music share on the slug, and make sure that you have process_m3u set to 1 in the config.
You could do a logon script or startup item to copy that over when you log in on the windows side. (or even a “scheduled task” to copy that file over periodically).