I think I nailed it! I now have Podcasts on my iPhone 3Gs 3.1 in the order I want them to be after syncing with iTunes 9.0!
I first tried the steps on this page:
http://www.gotknowhow.com/articles/how-to-get-podcast-playlists-to-sync-in-itune s-9.aspx
This didn't help me, so I deleted all my Podcast playlists, synced my iPhone, recreated the playlists, synced again... still Podcasts sorted by nothing.
Then I created a new Playlist 'test 1' (not a smart playlist) and dragged all the tracks from my iPhone podcast playlist into the 'test 1' playlist. Synced the playlist 'test 1' to my iPhone and it contained all the Podcasts in the correct order! But I missed the 'Playcount is 0' rule, so I created a smart Playlist with 2 rules:
1. Playlist = 'test 1'
2. Playcount = 0
Sorted the list by Release Date ascending and it worked as well!
Then I did the following as a final test:
1. Created a new Smart Playlist with the rule: Playlist is 'iPhone podcasts' (Live updating is checked)
2. Gave it the name 'a Podcast'
3. Added the column 'Release Date' to the view
4. Clicked the 'Release Date' column header twice (to sort by Release Date ascending)
5a. Right-clicked on the playlist name to open the context menu
5b. Clicked the 'Copy To Play Order' menu item
6. Changed the view to 'Cover flow'
7. Checked the 'a Podcast' playlist in the iPhone->Music->Playlists panel
8. Checked the 'iPhone podcasts' playlist in the iPhone->Music->Playlists panel
9. Checked the 'a Podcast' playlist in the iPhone->Podcasts->Include Episodes from Playlists panel
10. Checked the 'iPhone podcasts' playlist in the iPhone->Podcasts->Include Episodes from Playlists panel
11. Synced my iPhone
Now the 'a Podcast' playlist contains all the Podcasts from the 'iPhone podcasts' playlist in the order I see them in iTunes. The 'iPhone podcasts' playlist was my original playlist that worked with iTunes 8. It contains all my Podcasts with Playcount = 0.
I'm not sure if all the steps are necessary, but this worked for me and I'm not going to screw things up by seeing what does and doesn't work! 😉 Let me know if it helps you out!
Good luck!
Ilan Shemes