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[goatherder]

...if you do at all.

I'm looking to have a do-over as far as the Mac side is concerned, clear out my Music library and copy over everything from MC again, and perhaps at least make an effort to keep them in sync this time.

I am subscribed to Match, if that is an additional complication for any reason (and being a Match subber is one of the main reasons why I want to keep both libraries in sync).

[HaWi]

... I don't anymore.
I used to have a single 'Music' folder that I accessed from iTunes, DS Audio and MC. Turns out after a while it is a disaster because they all modify the media files if you let them and then the others get confused. I used to mainly use iTunes to modify media files (tagging) but switched to MC for good. I kept using Tunes for a while trying my best not to let iTunes modify my media but it turned out not to work too well.
Now I use MC exclusively to modify and manage my media. I completely abandoned Apple Music (and Match) and even bought most of the tracks that were .m4p (and couldn't be played in MC) again from other sources, in better quality.
My recommendation would be to keep two separate physical media collections for AM and MC if you want to keep using Match. Keep the AM mostly in the cloud and import tracks into MC when you get new ones.
The fact is that MC is vastly superior to AM (and most other media management tools) and thus there is no reason to use anything else. Except, of course, if you have historical commitments, such as a Match subscription. In this case it's up to you to decide how valuable that is to you.
After some thinking, I decided that the power of MC was much more important to me than the perceived convenience of Match. Since I switched to MC my Music collection is in the best shape it has ever been in since its inception about 20 years ago.
Good luck!
Hans

[goatherder]

Even one-way (MC->AM) would be better than nothing.

[HaWi]

Of course, it's possible but you have to monitor closely what AM does to your media files. You also need to decide which one you want to use to organizes the tags and media files and then make sure the other one doesn't interfere.
What I did originally was to import all the media (audio) into MC from iTunes. Then I managed all my tags and files in MC which led to iTunes not finding a lot of files anymore. Then I deleted the entire iTunes library (not the media files, of course) and re-imported into iTunes. However, every time I did some major work on the library in MC, I had to do this deleting and re-importing in iTunes, and after a while I just got tired of it and stuck with MC exclusively.

[goatherder]

Yeah - I was hoping to dispense with the "delete everything and re-import into iTunes" bit.

I guess maybe not.