Bug - Unable to get certain achievements

[Cosmickly]

I've completed the game once and went for another run to unlock more achievements. In my first playthrough I could unlock achievements just fine, and would even see a Steam popup whenever I made progress in some of the achievements (e.g. trying a new drink for "A Real Connoisseur").
Throughout my second playthrough I could still get some achievements (like "The Saga of the Schoolyard Sentinel"), but all the ones where you have to do something X amount of times aren't unlocking. I even made another new save and drank 20 times for "It's Fine If You're Already Dead", but nothing. No unlock, and no progress popup. I've also tried reinstalling the game, and swapping the save files around. Anyone experienced something like this?