Can't Download Any iTunes Match Songs in Library

Hey all. I'm having a problem with my iTunes Match and hoping somebody could help me figure this out before bringing it in to the Genius Bar.

I've been paying for iTunes Match since mid-2014 and have been continuously billed every year with no lapse. I assumed everything was fine because my iPhone 6S has the ability to download/stream every song from my library. Bear in mind, I very rarely use iTunes or even the music app on my phone (mostly listen to podcasts on Overcast or Spotify), so I don't keep close tabs on this.

Skip to the other day when I opened up iTunes on my early 2015 15" MacBook Pro (running Mojave) and noticed that all of my songs in my library were grayed out, and when I tried to click on the cloud icon or right-click to download, nothing happens ("Download" wasn't even an option on Right-Click). I also had recently added a new playlist and nothing synced to my iPhone Music app.

I'm not sure why this isn't working as intended. As far as I know, I haven't changed anything since I originally signed up for iTunes Match, and I used to be able to download songs or stream them in iTunes. I *did* notice that I don't have iCloud Music Library enabled in my iTunes preferences, but admittedly, I'm a little gunshy to activate it, as I remember I lost all of my playlists when I first activated iTunes Match in 2014 and I worry that checking that box now will wipe all my songs since it seems my Library is empty?

I included a picture below to show what my Library looks like but any advice on how to fix this would be much appreciated. Notice the cloud icons and everything are greyed out.

Thanks in advance!