Damn wish I would've seen this sooner. I've used that mp3tag program too but if you get musicbee working it's much more seamless and automated. If you look at the pic I posted, at the top right you have to choose your device, in this case the ipod classic. The settings you choose are device specific. Then on the bottom left you must choose "copy to the same folder as the music file" and put "cover" in the box for file naming. Check the box for "resize artwork to 300px" and you're good to go.
No problems mate. ;)
Using mp3tag again actually rekindled my love for the program. Sure, a program that has better automation probably works faster, however, musicbee is somewhat too full of functions for me to properly use.. ;) Plain and simple, that's all i need. Mp3tag and automatic cover tool fit the bill. Might be a bit more work, but if it saves me from tuning a program to my likings for hours and building a music database that i'll probably never use (oldskool Winamp all the way over here..) It's worth it for me anyways, spend waaaay to much time at work fiddling with software settings already, hahaha. ;)
@stealer: Youtube works wonder for questions like these..
Edited by Xxxneoxxx - 1/13/13 at 7:23am