I can’t ml_ipod to work smoothly. The live smart playlists wasn’t working out, and the smart playlists weren’t matching up in the iPod and Winamp. Also, importing the iTunes database didn’t correctly import the last played times. It might be that plugin’s problem, though (because ml_ipod is a completely different entity). I didn’t investigate further than that, because it didn’t matter too much for me past that.
So, I’m back in iTunes. I’m not kicking and screaming, but I’m still rooting for Will and whoever else is helping him. If there’s any consolation, Will Fisher (developer) is really nice – at least from my interaction with him in the forums today. 🙂