Problem with iTunes/iCloud "waiting" status

Alright, let me try to break this down. I've looked everywhere on how to fix this and have tried most of it I think. I've tried signing in and out of iTunes and iCloud. I've done the update library thing.

So I have hundreds and hundreds of song that say iCloud status is "waiting." These songs are greyed out and can't be clicked or anything. The cloud to the right is dotted or dashed. Basically all of the songs like this are ones that weren't purchased or something from a store. They are mostly mixtapes I downloaded years ago that are pretty old songs. It's also all of my music that I used to make and master in Logic Pro and then send to iTunes. So basically it's a lot of stuff I'd like to have.

This happened once I had to restore my computer, apparently wiping all of these files. The problem is, I thought iCloud and iTunes would save these songs. They're obviously still there, but how do I get them back and playable?

I have an update available on iTunes so I guess I'll do that soon. But there has to be something else to do other than updating library and just signing in and out of iTunes. Did I lose these songs forever because I did a restore? What's the purpose of iCloud then? Ugh.