One of my favorite game publishers, this is wild (and not the Outer kind of wild). I’m super curious if the entire staff will start their own publishing company (which I imagine is harder to do without the financial backing of a billionaire’s daughter) or if they’ll split off and go their separate ways.
I’m also very curious if this will start changing the kinds of games Annapurna publishes or if they’ll still take interest in odd and niche games that need a publisher. I wish I knew more about the dispute here but time will tell what happens next at some point.
My best guess is the Tales to Tremble By scary story collections:
Each story had some creepy art by Gordon Laite:
A lot of this fits with your descriptions from the best of my recollection.
Edit: Removed paragraph about potential third scary story series containing spider egg story, just realized that one was from Scary Stories to Tell in the Dark 3, so Tales to Tremble By and its sequel is my only guess here.