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It has to be 15 events on the same savegame without reloading. I mostly did the graveyard party since it is the cheapest one in terms of reputation stars.
You can do multiple events after each other, but make sure that your character sleeps afterwards, so they're saved to the savegame.
But simply saving after each party and then loading later worked fine for me.
Btw: if you want to play safe and make sure that Yorick always has some food in his inventory, it is very quick to make onion rings in the new kitchen. You can get the oil from Dig. But I don't think that's required at all.
EDIT: I just found a Stranger Sins achievement guide, and I see a pattern now, ONLY my SS DLC achievements are unlocked, and the rest remained locked. I'd downloaded the bundle for Halloween, so I've never had a vanilla version of the game installed. All my vanilla achieves (and possibly the first expansion content if I judge the title page right) failed to unlock when I did them.