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Man, that's a sweet deal.
Is your Steam overlay disabled by chance?
Start a new game in hardcore mode and then complete any task, the easiest and fastest would be to find your second shoe at the beginning.
You then should get the "Venture into the HARDCORE" achievement.
This takes about 5 minutes, if you get it you know its your other save that wont register achievements.
If it doesn't, try to "verify integrity of game files", if that doesn't work, re-install the game, if that doesn't work, contact a support team of steam and/or the game's support team.
If you are not 100% sure, try to get the "Palerunner" achievement, should be possible for you now at 30h+ playtime, on youtube you can find a quick and easy guide to get this achievement and i doubt you would have gotten that achievment while just playing the game.
https://discoelysium.fandom.com/wiki/Palerunner
https://discoelysium.fandom.com/wiki/Venture_into_the_HARDCORE
This is the reply from above I was referring to:
Yeah, I saw that. I'm hesitant to play further into the game if this is broken. I'm a 100% chaser, so if one achievement is broken but another pops, then it messes up my 100% record. I'd rather drop it if this is broken. I appreciate the suggestions, though.