Here's what I do. I made a new playlist then just keep adding songs to it as I see fit. Then, after I hook up the ipod, I go into preferences and check the name of that playlist to be automatically updated. Now, every time I hook up my ipod to my comptuer to recharge, it automatically adds any new songs I've added to that playlist.

I want to eventually have all my music on my comptuer in my ipod, but the file names are all messed up. I have a feeling it's going to take months to go through and rename everything. I've got 5,000 tracks. Yikes! A bunch of them are nothing more than snippets of movies, or free songs I downloaded from websites that I'll never listen to again and all that crap. But I know I have at least 4,000 good songs. So I'm going to really have to redo the whole thing. Ugh.