To cut to the chase: is there any easy way to have emplode "synch" with a directory structure?

I feel like the most intuitive way to organize my mp3's is using a nice directory structure. like mp3\NewMusic\Kent\songtitle, or mp3\Rotation\Radiohead\songtitle, where "NewMusic" and "Rotation" are my "playlists".

I know I can just drag the entire \mp3 folder to the playlist folder on the empeg, and it will create playlists in a similar heirchical fashion. BUT, this only works once! If I delete all my playlists and drag \mp3 again, it copies every single song to the rio again, making duplicates. If I just drag the \mp3 folder without deleting the playlists, sure it detects duplicates and adds new stuff only, but doesn't delete anything I may have removed on the desktop.

Maybe there's something I'm missing -- is there any way to do this? It would be great because I manage songs on my ipod in a similar fashion, and it's just painful to manually go in and figure out what I've deleted and added and synch by hand.

If there's no way to do this, I'm willing to write my own win32 synchonizing program -- would this be possible? are enough methods exposed to communicate with the rio in win32?