Managing Music

Ok, so:

TiVo HD and iTunes music managing - all music is .mp3 files.

I've got TiVo media manager / desktop software linked to my 'iTunes' music folder. It will allow me to access all the music individually, ie: by artists. What's the fix to just have a gigantic shuffle? When I try to just play from the iTunes music parent folder, TiVo gives a connection drop error.

Any thoughts? I'd like to put my 300 GB of music on shuffle for TiVo!

Thanks!