I tried to resync but it didnt.. I ended up just going in through my computer and taking copying them to the harddrive, then when you load them back into iTunes, it renames them back to artist - song.mp3.. only bad thing is it just puts them in weird folders while it does this..
I'll try it out again if I ever have to
Yeah trying to do automatic syncing will drive one crazy, unless you do the playlist thing. For as much as I like playlist, I hate using that method to sync my iPod though. I actually found a way to do it automatically, but by putting a check in front off all the music I want it to sync. If I want to remove music, I just uncheck it and resync and BAM it is gone. The only issue with this is when you add music to iTunes if you don't want it on the iPod, you have to remember to go uncheck it because the next time you sync it will add it. I do this with holiday music and it just works well.
The other way of course is to manage your music manually and then YES you simply drag and drop what you want on it. Or you highlight the music on your iPod you no longer want and hit delete and it is gone.
I have the opposite opinion of the playlist method. It lets me add what I want to add, if I buy a new album from iTunes, and I want to listen to it all the way through, all I have to do is add it to the playlist for the iPod. In a way it's drag and drop but in another way it's totally automatic, since it deletes what was on the playlist and adds what is there now. I tried checking and unchecking and it just got complicated. It's nice for Holiday music for my 80GB iPod when I don't want it on there, but not much else.