Ipod sync transfer fail strangeness

[spinningdoc]

Please point me in the direction of any posts on this one - I've had a poke round and I couldn't find any.

I'm syncing my iPod classic with the latest version of Winamp on Windows XP, having switched over from iTunes. Pretty much everything is fine apart from Winamp not syncing some tracks that I want synced, and still trying to sync things gone from the Media Library.

Non-syncing files are in the same directories as syncing ones, added at the same time, from the same rips - they just don't sync. The track will always get synced successfully if I use 'Send To:', but not when I use the 'sync' button, which leads me to think it's not down to corrupt files. I'm using the ipod plugin that comes with this version of Winamp.

What I've tried so far:

- Clearing the ML and rescanning. (I've tried this frequently, after doing most of the other things on the list)
- reformatting the iPod and resyncing the mp3's to it. This worked for about 90% of the tracks
- checking metadata for unicode strangeness
- checking they're mp3's not wma's

In the transfer list (which is just a string of fails), Winamp seems to be extrapolating track titles from the folder structure, coming with oddness (I can go into this a bit more if anyone thinks it might be a possible cause).

Also, when I sync, all the failed files are counted as 'not on the iPod' though many are. It's extremely confusing.

My only thought is whether it's possibly to physically delete the library file that Winamp says it's clearing because I suspect it isn't clearing it, and forcing Winamp to rebuild it.

All thoughts gratefully received.