Keychain not working - logged out of everything after restart

Hi all. I had a problem about a week ago when I restarted my computer, and suddenly I was having an error message pop up when I tried to sign in to iMessage. I spent about an hour on the phone with apple care, and we messed around a bit: deleted some items from the keychain, restarted a few more times, and eventually it mysteriously decided to allow me to sign in. Note that we specifically did NOT clear my whole keychain, just deleted a few specific items (I can't recall exactly what, sorry). But afterwards, I found that I'd been logged out of every website, and none of my passwords were remembered. Every time I signed back into anything, I was asked if keychain should remember this password, and I always clicked yes. So they should have all been saved, even if they were somehow erased the first time.

Today I restarted my computer, and the error came back with iMessage. So I went into keychain and just deleted just iMessage, restarted again, and it decided to work. Idk. And yet all of a sudden I've been logged out of every single website all over again and none of my passwords are remembered. And when I open keychain access, it looks like it has a whole list of sites and things still in it. But it's not prompting any of the passwords or anything for any website I try. I suppose this isn't that big of a deal, but it is honestly a pain in the *** that I apparently have to now manually login to every account I've ever used on the internet (I've definitely lost a few passwords and have had to reset so many in the past week, the first time I went through this), and that this will happen now every time I restart my computer, apparently??

I feel like there's a disconnect between my keychain, which has all these things saved, and actually recognizing them and applying them. I use google chrome, if that's relevant. Any idea how to fix? Thanks.