IOS – ITunes Match: syncing smart playlists that reference other playlists

There are a couple of potential solutions to this problem. I say potential because everyone's listening habits and needs are different, so your mileage may vary. Here goes:

The Smart Playlist problem is not new, and certainly not unique in your case. There seems to be an overall problem with Smart Playlist syncing through iTunes Match (1) across different devices, (2) with any expediency (usually takes >= 48 hours), and (3) with respect to honoring certain rules (e.g., number of songs allowed). Another common theme seems to be that "nested" playlists cause even more of a problem than standard Smart Playlists. Nested lists are those that are created when you use your option key to turn the + into an ellipsis (...), which creates a sub-rule for your master rule.

Solution 1: Dumb it down

Create a standard playlist (Dumb) and give it the same name as your Smart playlist. Copy the content from Smart to Dumb. Sync your device, computer, whatever. Rinse, wash, repeat for each Smart Playlist you want to have properly represented on your other devices. This works.

Solution 2: Really Dumb it Down

Do your best to avoid the aforementioned nested playlists. This may require you to build several smaller smart playlists with limited criteria. Not the easiest workaround, but we're going for functionality here, right?

Solution 3: Really make your "Recently Added" folder songs that are "Recently Added"

For your "Recently Added" folder, tack on just one more rule to force songs added after a date, rather than only within the last two weeks (see pic below)

So, I hope this gets you at least a little closer to your goal. I tried to add as much info as I could here since, one more time: everyone's listening and categorizing habits are different :-)
You may find other variations on these, but do realize that, at least for now, this is a server-side problem and workarounds like these represent the best available solutions.

If the playlist sync over but the podcasts fail to play, it could be that you have your iPod shuffle set to "shuffle songs". You must switch to "play in order" for it to work.

From Apple Support:

Playing Audiobooks and Podcasts on iPod shuffle

When using iPod shuffle (1st and 2nd generation), if iPod shuffle is set to shuffle songs it will play all the audio files on iPod shuffle except audiobooks and podcasts. To play an audiobook or podcast, set the switch on iPod shuffle to play in order .

When using iPod shuffle (3rd generation), podcasts and audiobooks will not be played when content is played from All Songs. If content is played from a playlist synced from iTunes, audiobooks and podcasts will only be played if the iPod's switch is set to play in order . In addition to playlists synced from iTunes, iPod shuffle (3rd generation) will create a special playlist for each audiobook synced and one for podcasts. When accessing these special playlists, audiobook and podcast content will play whether the iPod is set to play in order or shuffle songs . Podcast are sorted by alphabetical order and then by episode date.