Q: Smart playlists not live updating on Ipod classic

Thanks for the suggestion(s).

I edited my existing smart playlist to your parameters (which I prefer, BTW... Keeps me from modifying album names.), synced my iPod, reset my iPod, played an entry in the smart playlist to the end to increase its play count to >0 and it did not live update, unfortunately.

Wow, that did it for me. Changed the dropdown selector to All Media and the playlist is updating on the iPod again.

Here are my latest findings on this topic...

In troubleshooting this ridiculousness, I have created three Podcast smart playlists on my desktop iTunes instance.

Here are their names:

Here are the parameters for each:

(note, on the above, if I choose "Match all media" and specify "kind is podcast" and "plays is 0" rules, iTunes automatically modifies the smart playlist parameters to the above (e.g. match podcasts for the following rules))

Upon synchronization with my iPod classic, the !MediaIsPodcast-Plays0 smart playlist isn't even accepted by the classic:

!Podcasts2 does not live update on the classic (hence the count of 34 songs versus 33 on !PodcastsSmrtPlylst2016).

But, hooray, !PodcastsSmrtPlylst2016 does live update on the classic!

!PodcastsSmrtPlylst2016's sort order does not synchronize on to the classic, so I cannot listen to Podcasts in the order I would like, so, once again, I'm left with inconsistent/lost-functionality results. 

IMHO, Apple creates a !@#$ waste-my-time customer experience by failing to add a top-tier "device" parameter therefore allowing the customer to only create logic that is compatible with the device they are (or are not) synchronizing with.