Syncing between Winamp and iTunes isn't the problem. It's syncing between Windows and Mac. It's not officially supported, but by judicious research, you find out that you can do it, IF you format the ipod for Windows. Of course I formatted for Mac. So I had to "restore" which is apple double-talk for reformat. Hint: Unless you're hiding serious product deficiencies, you don't refer to a reset to factory settings as a "restore." And Earth doesn't have homeless [people].
I'm set up to use manual syncing on both Winamp and iTunes. When autosyncing it deletes everything from your ipod that isn't on your local machine (at least from what I can tell and since I have different songs on different computers but want the ipod to have some from both locations, manual sync works well.
So there you are.