So, I don’t know if something changed in iOS or in iTunes Cloud Library or what, but now the cloud smart playlist thing is working a lot better now; at the very least, my cloud-synchronized smart playlist is at least doing the proper album shuffle on my phone.
It still doesn’t seem to be updating what’s in the playlist based on what’s been played/skipped recently, though. But it’s hard to tell if that just takes a while for the play stats to get updated and propagated or what. To be fair this is a hard problem.
Meanwhile, I also finally upgraded my laptop to Catalina. The new Music app is taking for-freaking-ever to sync over my library. But at least it claims to support it, after clicking “Please don’t sign me up for Apple Music” about a dozen times, and then once again saying “yes I’m sure” when I tell it to turn on syncing my actual library. But this also gave me an opportunity to see how much of my stuff is broken; the Native Instruments installer is working now, and while NI still doesn’t recommend upgrading, all of their software that I use seems to be supported.
Unfortunately, my desktop’s audio interface isn’t currently supported on Catalina, so I won’t be upgrading that any time soon. Presonus have said that they will be releasing a Catalina update for it after all (after years of saying they wouldn’t release any more updates) but there’s no timetable for it. If there’s no update in, say, 3 months, I might have to start looking into new audio hardware, and that’s expensive and I’ve yet to see another audio interface which supports (or at least advertises) the hardware submix functionality that I use on the FireStudio. I got used to that when I set up my Twitch setup but have found it to be genuinely useful for keeping my headphone and speaker mix separate regardless. It’s nice not having to deal with muting my connected microphones every time I switch to my speakers.