I have what may be another workaround, or perhaps not. I'm still testing it out.
Just before you reconnect your iPod to computer, jump to the previous track just listened to, rate it one star, then advance back to the track currently being listened to, pause, then connect.
It may be voodoo, but it seems to work most of the time. As a backup, I always add my currently listened to tracks to an On-The-Go playlist just before connecting, as I still frequently find that the list of tracks just listened to gets wiped upon connecting.
Please, Apple, fix this issue. This has been going on far too long. All issues related to music playback should be the first things fixed in the next iPod update, I can wait for copy and paste and other fixits.