Tough to say, but my mind defaults to Danganronpa V3, since I went for every achievement and a decent amount of those are based around doing the side modes which include a luck-based board game and a weird turn-based RPG. If you don't get lucky while building your characters or just really know how to cheese some of the mechanics it can become incredibly frustrating. There's also the Monolithic achievement which is for earning the best rank in a minigame, and it's the kind of thing people have created solvers online to try and do for you. Of course I only found this out after I got the achievement in the first place by pure luck.
I'm sure there's something else worse I've gone through, like a "go through the entire level to try to get a rare drop at the end with a 1% chance". Monster Hunter and its plates or gems are what come to mind there.
If you could only eat at one restaurant for the rest of your life, which would it be?