svferris: This might be a stupid question, but I assume that when you say you're cleaning up all the MP3s using the software, that you'll need to upload them all again to the player.

Irrespective of any undiscovered new V2 editing capabilities, this is what I'm doing (One of the bonuses of having a "spare" -- start with a clean slate). I have a 90GB RAID-1 Linux box that is my repository (I rip with grip/LAME/cdparanoia on that box) and I point Tag Studio on my Win2K machine at the mp3 directory on that box. The long term goal is to have them both organized in the same way, so that when I rip something new, I fix all tags right then and there, put it in the right place to begin with, then move it to the same spot on the Empeg/s.