ITunes 8.1 breaks syncing with 2nd gen iPod shuffle

Question

So, I downloaded iTunes 8.1 as soon as it came out as all the new features seemed pretty benign, and I've never had issues with any iTunes update going all the way back to 1.0. However, the 8.1 update rendered my 2nd gen shuffle no better than a $5 MP3 player.
Keeping in mind I use my shuffle primarily for listening to podcasts, here's the issues:
+1) dragging files to the iPod that already exist on the device+
8.0: pops a dialog warning that some of the items are already on the device and gives you the option to skip those ones and copy the rest. I use this all the time as I just do a select all and drag everything in my Podcasts list to the iPod to get new stuff onto it
8.1: it gladly copies the duplicates onto the iPod again
+2) order of podcasts when added to the iPod+
8.0: podcasts get put at the end but when you disconnect, they get moved to the beginning of the play order on the shuffle and are arranged in the same order as the sort set on your Podcasts list (in my case, ascending Date Released). This was great as all the podcasts would end up right at the beginning of the shuffle in the order I wanted
8.1: podcasts get put at the end and stay there, in whatever order they were in from the location I dragged them from (i.e. the literal order they appear in the Podcasts list. So while in 8.0 they'd be arranged in date order regardless of whether different podcast subscriptions were mixed together, in 8.1 they were placed into alphabetical podcast order, subsorted by date)
+3) automatic removal of deleted podcasts+
8.0: a podcast deleted from the Podcasts list that's also on the shuffle will immediately cause a sync event and remove it from the shuffle
8.1: no sync event, deleted podcast stays on the shuffle until manually removed
+4) ability to play songs from the shuffle in iTunes when the shuffle is connected+
8.0: double-clicking a song that's on the shuffle by selecting the device and then its Music tab, plays it (and also causes immediate and constant syncing, which is weird, but also expected)
8.1: double-clicking a song has no effect. Selecting a song and clicking iTunes' play button does nothing
The problems are occurring on my Mac Pro. I initially upgraded to iTunes 8.1 via Software Update, but tried reinstalling via the standalone installer. No luck. I also tried restoring the iPod to factory settings twice with no luck.
I also did some tests on my MacBook Pro which still had iTunes 8.0 on it. The same "correct" behaviour was encountered on the MBP. As soon as I upgraded to 8.1 via the downloaded installer, the same "incorrect/broken" behaviour was encountered as on the Mac Pro. I restored the iPod in iTunes 8.0 and 8.1 and that still didn't fix the behaviour when using it under 8.1. Additionally, on the MacBook Pro I removed the iTunes library and started with a fresh one just in case there was something funky with it.
Anyone else having these problems? I know at least one person whose 2nd gen shuffle works with 8.1 as it always had, so I'm not sure what's up with my shuffle.

Answer 1

I'm having most/all of the problems mentioned here. As far as manually ordering tracks, that doesn't work either. As near as I've been able to determine, tracks are played in the order they were put on the Shuffle, no matter how you order them in the list. The only way I've been able to get them in the order I want them is to put them all into a separate play list, set the desired order, delete everything off of the Shuffle, then copy the whole play list onto the Shuffle. By the way, deleting tracks off of the Shuffle doesn't seem to generate a Sync event by itself. While the list window shows the total size of the items in the list at the bottom (and it decreases when items are deleted), clicking on the Settings tab shows a bar at the bottom showing the same amount of space being used before the deletion. You have to move something else to the Shuffle to make it Sync.
Also, the one problem I've experienced with 8.1 that I haven't seen anyone else mention is connecting the Shuffle and having it show files that hadn't played as having been played and other files that had played not showing as such. For example, say the last thing I did before disconnecting was to put 20 new files on the Shuffle at the top of its list. It will play them last because they were the last items added. But when I reconnect after playing 20 or more tracks, the list shows the top tracks as having been played including those 20 tracks that I hadn't gotten to.