I rip library books (usually 6 - 10 CD's) each CD as a single file. For instance, I have the autobiography of actress Teri Garr as 6 files: GARR1, GARR2, etc. I can't use numbers for more than 9 files as my player reads 1, 10, 11,and then 2, 21, etc. so I use alphacoding for longer books(GARRk, GARRl, GARRm etc.). With 28 CD's I'd use GARRz, GARRza, and GARRzb for the final three. I drag and drop them when I'm done.
Or are you trying to sync all those files somehow?
I have a 28 disc book that I want to listen to on my Zen Microphoto. All of the tracks show up out of order listening order, all the Track 1s from each disc are sequenced first, then the track 2s you get the idea. If anyone can suggest a method to organize the files, I would appreciate it. I did not think of this before I started copying the cds. The longer books that I digitized from casettes, no track numbering was involved. Thanks!