Check out the ml_ipod plugin if you use winamp (newer versions of winamp actually have ipod support although I prefer ml_ipod). I've never used itunes and my ipod is 4 years old. It's pretty much a file browser window where you can organize the music on your pod. Fairly easy in my opinion. Maybe not as easy as dragging and dropping on chipods (which I own aswell) but must easier for file searching and organization as well as making playlists. Of course this is pretty moot if you don't have id3 tags which I don't know if you have since you're ripping from vinyls. They do show up via song titles but id3 tags really do make organization easier. Also, this plugin can rip music from your pod to your hard drive. There's other programs out there that can do the same but this one was the first free one I could find since way back when.
http://www.mlipod.com/