I managed to get the database updating successfully with the simulator so thank you for your info!
That said, I've have been doing a full Initialize Now pass which takes about 25 minutes (would be nice if this thing could go faster by utilizing more cpu cores or something). Going forward, I'm hoping the Update Now pass is all I need but I haven't tried it yet.
I also noticed that the album art is rarely working. Sometimes it'll show but more often than not, it won't. Is that normal? In case it helps, I embed all my album art images into the mp3's themselves.
Getting playlists working involves a bit of thought, but I'm sure you can work that out for yourself.
I found a converter program that'll get the playlists to work now that I'm back on the iTunes/iPod syncing method.
I would love to somehow write a script that automates all these steps I'm going to have to repeat every time I want to update my iPod.
BTW, I love your name "Frankenpod" as that is what I called my modded iPod for many years.