Windows – How to fix smart playlists with live updating to update again in itunes 11

I think the best option you have is to recreate your super playlists as a single more complex playlist.

When you are editing a smart playlist you can option click the '+' button (turns into '...' while you are holding option) and this creates a subgroup that can a condition of it's own.

This playlist picks music based on rating and last played choosing higher rated tracks more often:

One technique I used in some playlists was to put NSFW tracks in a playlist and then build other playlists to exclude NSFW tracks. Putting tracks in a playlist is an easy way to add additional information about them without having to edit the ID3 tags. That doesn't work with these more complex smart playlists.

You will have to put additional information like that into the ID3 fields. You can use the comments block for this, but I don't like to do that because I like to be able to add this kind of flag to multiple tracks at once and I can't do that as I may be losing comments already entered. Genre works if you're willing to use that instead. Any field will work; as I don't have tracks that use grouping I used that for my own NSFW tags.

One slightly more complex place to put these kinds of tags is the 'Category' field. iTunes keeps a category field but doesn't show that field in the editing UI so it's normally not used for anything. Doug's Applescripts offers a script that will let you edit this field. (script and instructions)

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.