iTunes, Songbird and iPod Troubles (and Joy)

So I have an iPod. I’ve had one for a month or two now, since my last MP3 Player died and it turned out Creative discontinued that particular model.
Apparently people don’t want lots of storage.

…so I have an iPod now. I like it, and I love Song Summoner. I still don’t quite like how it looks as much as the Creative Zen, and the clickwheel is at times overly sensitive or utterly numb, and that can be annoying.

I don’t like iTunes, however. It’s slow, and whenever it’s running it tends to drag everything else down with it. Editing certain tags for songs – such as track or disc numbers – is also complicated, as you can’t quite do that from the list, like you can with song names or album titles.
It also absolutely refuses to pick up on ratings from the iPod, and automatically overwrites them all. ‘Liked that song from Soma Bringer when you heard it on the bus? Too bad! I’m going to erase your rating and you’ve forgotten it already!’
Nothing I do seems to let the iPod keep its ratings; some people talk about setting it to sync manually only, but that still doesn’t really work. I still lose my ratings, and whilst iTunes pushes to be a primary media player, I like WinAMP more. It plays all of my music, sparse DRM’d files aside… and would probably play those, too, with a little tweaking.

So. Songbird. Songbird is supposed to be compatible with iTunes and iPods, so I downloaded it yesterday, meaning to give it a try.
I love Songbird. It still probably doesn’t play everything like WinAMP will, but it works so much faster than iTunes, and is really handy for working on a song’s tags. I just spent a few hours playing music in Songbird rather than WinAMP, and it wasn’t inconvenient at all.
Songbird’s supposed to be able to work with iTunes and iPods, anyway. It does successfully pull the library from iTunes with no problem whatsoever. It also detects songs on iPods, and happily pulls ratings from THAT, instead of substituting its own ratings of currently-nothing.
However, it completely fails at syncing with an iPod. The attempts I’ve made thus far have either been non-starters, or just locked up at some point. I’ve found nothing talking about this problem, and I can’t think of how to fix it, so for the moment I’m still stuck with iTunes for my iPod needs.