How do I get Podcasts working with my iPod Classic?

Since the last update, my podcast playlists are not syncing to my iPod in anything close to a usable fashion. The same playlist is still 80% functional in iTunes. Anybody have any ideas for a workaround?

What's the playlist? Before the update it was a smart playlist with two rules:

1. Genre is Podcast

2. Plays is 0

I also sorted the playlist by release date (sorting in iTunes would carry over to iPod Classic)

Now I have to select a media type. Selecting Music creates an empty playlist, selecting Podcast does not transfer to iPod, and selecting all media does not produce a sorted list.