I'm probably just gonna go with the 4Gb model. $180, and after completely combed my music collection I only found a maximum of 3.18Gb that I'd actually wanna listen to on the go, and that's assuming I'll keep all the complete albums I plan to throw on it, which I don't think I will.
If worst comes to worst, I can always buy a Mini-SD card to expand it. :3
Now to figure out how to keep my playlists or figure out a way to easily make custom (not just a single folder) playlists for it.