Q: iTunes not authorizing for content

I truly hope someone can help! My husband and I are both having this trouble....

We are both running Windows 10 on HP laptops, and we both have the most updated version of iTunes. The only difference between us is that I didn't have this problem until after my laptop updated some BIOS files last night.

When we both try to sync our devices (I'm syncing an iPod Classic, he's syncing an iPod Touch), we are receiving messages that we need to authorize our computers to play certain content -- not all content, just some. The last time we BOTH synced our devices, everything worked fine -- everything was authorized, the sync worked with no issues.

I've re-authorized my computer more than once in the ways: from the iTunes Store menu, and from the dialog that pops up when iTunes recognizes that some content isn't authorized. I have more than one Apple ID (not sure how that happened, but whatever), but all my accounts have the same password. Re-authorizing does not resolve the issue, and some content just won't transfer back to our devices. My husband has lost ALL his Audible books, I've lost more than 200 songs and a few older Audible books.

Is anyone else seeing this, and do you know how to resolve the issue?