iTunes purchases dating back to 2005; how to get permission to listen to them?

What is an efficient way to be access old purchased music?

Currently, I have to authorize my computer to allow songs for a Buch of old usernames. For context: I have an iTunes library (~6k songs) that includes songs purchased as far back as 2005. I'd like to be able to sync and play all of them on my latest phone, but am have trouble dealing with the permissions on about 20% of them.

The songs are purchased by family members under at least 2 email addresses. If I log into iTunes using those email addresses, then authorize the computer to play songs purchases by the user, that resolves the issue.

Unfortunately, I can't display the "Purchased By" field in iTunes; I'd like to be able to see all the email addresses I need to reconcile without having to click on each and every song to confirm. I don't know exactly how many there might be. Any thoughts on how to do this efficiently, and what I can do to avoid having to do this again when I get a new laptop or phone?

I'm not confident that iTunes Match is the right solution for this, but maybe I'm wrong about that?