Okay, so the problem has come back now, and I'm *not* running Little Snitch, but Ad Guard is installed (albeit not running right now in an attempt to get things working) and I'm still having issues. So I think I'm going to have to ditch AdGuard. Frustrating for sure, but better than things not working.
I tried disabling a bunch of things in the AdGuard preferences and it still doesn't want to work. It's not worth the aggravation that's for sure.
Update: uninstalled Ad Guard. Still haven't reinstalled Little Snitch. Still having issues with it uploading. Every time I try to upload something the activity just spins. Eventually an error message about being unable to return Genius results comes up, and then things stop and in the little status bar at the bottom of the screen it says "an error occurred".
This is especially frustrating because once I got things working last week, I was able to upload/match a couple of albums to my library no problem. Nothing has changed since then (I was running AdGuard at that point). So now I don't know if this is an Apple Music issue or what.