First time with Android, need help with adding media
I guess since no one else answered, I'll post what I ended up doing as an answer.

The solution that worked best for me was iSyncr. It's a Mac/PC app that acts as a middleman between iTunes and your device, so you can sync all your iTunes music, playlists, and song data.

It wasn't perfect or free, but it was what worked the best for me.