How can I fix Music Match issues with Mac?

I purchased Music Match back in December. I had used it years ago, and it worked great. However, it doesn't seem to work well with the new Music app on my Mac.

After purchasing Music Match, I loaded my entire library into the Music app and selected 'Update Cloud Library.' The "Updating Cloud Music Library" message in the left-hand corner has never finished.

When I check the status of my songs, I see that 5 are marked as "matched," hundreds are listed as "purchased," hundreds say "waiting," and a few hundred show "error." I have reviewed the documentation, and none of the errors seem to apply to me; these are old songs that are currently available on Apple Music. The songs that have uploaded don't show on my Iphone, which is on the same account.

Any thoughts on how I can troubleshoot this issue? Somethigns obviouly not working on the server side as its been a month or more now.

[Re-Titled by Moderator]