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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.
I'm not willing to commit, but I can't dismiss this one out of hand. I will need to track down a copy and see if anything gives me that AHA! moment.
Thanks!
More Tales to Tremble By is the only one so far I might be eventually talked into thinking is the one, but no epiphany yet. The low angle drawing of the house and the sailor peering over the railing feel familiar (particularly that greenish wash over the sailor one), but they don't quite match the admittedly 35-40 year-old memory in my head.
The Tales of the Black Freighter vibes in it are pretty cool as well.
Oh, jeez. I remember reading that book in elementary school!
Thanks for the horrific trip down memory lane, ya bastid. Happy Halloween, too.
Man what a blast from the past. I haven't seen these in idk how long but my mom had these when I was growing up. I don't even remember the stories, but those illustrations were awesome and are among some of my earliest memories of being unnerved by an art style (along with the legendary Scary Stories and the Wizard of Oz series from 1900 with the W.W. Denslow illustrations)