I have a large digital music collection. Every file is correctly tagged and album art is both embedded in the file and available as a jpg in the album folder. All of that took about four straight days to do over the summer using MediaMonkey (which I now also use to sync my collection with my iPod Classic). Unfortunately, I have some DRMed music bought from the iTunes store and have to use iTunes to get them onto the iPod. But here’s what gets me – every time I transfer the DRMed tracks over, iTunes not only screws up the album art on the DRMed tracks, but also screws with the album art of other non-DRMed music. I then have to get MediaMonkey to repair the database on the iPod, a process that takes close to an hour.
Seriously Apple … iTunes has to be the worse media-management program ever. Its memory footprint is obnoxious, it is prone to seizing up, and it buggers up album art.
If you haven’t tried MediaMonkey, do so. It’s made my life a heck of a lot easier.