Problems with iTunes 8 for Windows, 1G iPod Nano

Question

i'm running iTunes 8.0.1.11 on my Windows XP Pro SP3 desktop, using it to manage my 1G iPod Nano 4GB software version 1.3.1.
ever since upgrading to iTunes 8, i've had a few issues with the way it syncs (or doesn't sync, in my view) with the iPod:
1: podcasts.
prior to iTunes 8, the two most recent unplayed episodes would sync and delete after play - "play" being defined as starting to play the podcast. i didn't have to listen to the entire podcast for it to be removed. this worked for me, because many of the podcasts i listen to are news highlight shows (some run almost 2 hours). i'm usually only listening to specific parts of the show, not the whole thing.
now, if i haven't listened to the entire thing, it doesn't delete. not only that, iTunes doesn't even automatically throw away listened podcasts from the computer anymore. not so big a deal on the computer (it's got plenty of disc space), but on the teeny-tiny iPod, it's a problem.
so now i don't listen to podcasts on my iPod anymore. is there a fix so i can take my news with me again?
2: music playlists.
prior to iTunes 8, when i synced a playlist to the iPod, it synced the playlist's +current order+. in other words, if it was shuffled in iTunes, it was synced to play in the shuffled order.
not any more. now, it only passes the "base" order of the playlist; i.e., whatever order it was "built" or manually arranged in. this is bloody aggravating. i don't want to listen to the same ten songs every time i hit play.
adding insult to injury, iTunes also no longer passes whether the playlist is set to repeat. so it stops playing after the last song. also extremely aggravating.
i realize that i can select "Shuffle Songs" in the iPod's menu. but since this shuffles all the songs on the device, it somewhat defeats the purpose of having bleeding playlists, doesn't it?
i realize Apple wants me to buy the newest, bestest hardware every time it comes out. but i like my old iPod, and it did exactly what i wanted and expected. until iTunes 8. so, any fixes for these issues out there?

Answer 1

This is a well-known issue. Apple changed the internal file names used with iTunes 8, which makes the ordering on 2nd generation Shuffles behave differently. There is no good workaround, apart from moving the files with a hand-crafted AppleScript program.
Apple has been silent on the issue, so nobody knows if we'll ever have a fix for it or not.