My question would be: are you switching completely to JR MC? I would recommend it but it's an important question. I personally scanned all my cover art in, 1K + CDs. It took a ton of time, obviously, but now I have nice 1200x1200 resolution cover art files.
This means full screen cover art looks great...however, copying songs to an iPod (or MP3 player) isn't as good because the cover art does not get downsized, so it can easily take 1GB from cover art alone--1MB per file average.