We got really lucky and managed to get it working again. We let steam run a check on the files (said they were fine), he turned off sync, and somehow it started working again. Don't know if it was dumb luck or if something actually fixed itself but worth a try. I'll post again if we run into the issue again. Right now, we've gotten another issue with Victoria not having a book we need to have for the zone we just went into.

I never remember having any of these issues with D:OS.