I've been playing for longer than I care to admit with automating my media collections.
Now comes news that Vinyl, a pocket-pc + win32 server is out and FREE.
Netremote/Girder/Media Center offer flexibility to the geekily inclined. Vinyl looks like the shrinkwrap stuff that just does.
"Vinyl was designed from the ground up to take advantage of your digital music collection. With Vinyl you can remotely navigate and control the playback of your digital media collection from your Pocket PC via a beautiful user interface that features album cover art throughout."
[Via Pocket PC Thoughts]