Yeah, its kinda silly.
You don't really have to do all that. Like Ayurox and jean said you can manually put you want in your ipod (assuming you're using a ipod). For me I created playlists of all the artist and just move the files into the playlists. It does take some times to do though. Currently, I have a 8GB ipod and my itunes library on my computer has about 14 GB. My Ayu's playlist took up about 3GB in my ipod, the rest are other artists and I have like less than 5MB left... lol. Sometimes I just rotate my playlist around.