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.

Just the fact that she's John Cassidy's (from Fallout 2) daughter won me over, but beyond that Rose of Sharon "Cass" Cassidy is a fun companion with great voice acting and dialogue that I repeat still to this day,

I'm pretty sure Neil Gaiman enjoys milk and cookies, he even wrote the story Fortunately, The Milk where a kid goes back in time to get the ever-important milk that his father forgot to pick up.

They're probably referencing another greentext from the perspective of a fast sprinting Elk that can't escape the long-distance persistence endurance of a bipedal human hunter:

In Stardew Valley one of the questions the game asks during character creation is "what is your favorite thing?" where you can type anything you deem fit for you (and your character). Without knowing why it asks this (or completely knowing why) means that an honest answer like "tits" can happen organically or specifically just for the chuckles.

Throughout the game, every time you find a Stardrop that increases your total energy bar, you are reminded of whatever favorite thing you entered at the start of the game.

At one of the lowest points of my life when i was locked into contract and couldn't make changes that would better my situation, the lottery was my anti-suicide failsafe. If there was a chance, no matter how small, that life could get better, I had to keep going.

I knew the odds and it wasn't about winning, just that twice a month I'd buy something that meant I had to keep going because statistically it gave me a chance to change my situation.

However, getting a false win at that time would have absolutely destroyed me.

Ugh this is me. I used to love spicy food but something happened a few years ago where it switched to just destroying me.

All it takes is a little bit and I'm sent into an uncomfortable, mouth-searing sweating fit for essentially the rest of the day. I've got bottles of alcohol-based mouthwash like Listerine stocked up since it's one of the few things that helps in those times when I accidentally get a hit of the ol' spicy stuff. Once I do that and wash off my lips with face cleaner I'm alright, otherwise I'm struggling to keep hydrated because I'll sweat for hours and hours.

Finally went to see an allergist that found a ton of underlying allergies and thinks that having all those go untreated is what increased my sensitivity overall. I'm currently getting the allergy immunotherapy shots and hoping that results in some regained resistance to capsaicin. It's super embarassing to be out and start sweating like a maniac when I get a bite of an appetizer I didn't know had pepper extract or one of those steaming plates of hot spicy stuff that sends a pepper cloud in my face and just leaves me drenched the rest of the night.

In the future, Activision will have completely taken over the bail bond industry.

Disco Elysium is a fantastic one. There are an insane amount of choices that shape how you go about the investigation of the hanged man and ultimately what happens beyond that investigation. Choices of who to side with, how to side (openly or playing multiple sides, etc.), choices that ultimately define what kind of detective you are (by-the-book boring, superstar douchebag, violent tough guy, Sherlock Holmes-esque genius, etc., including my favorite: Twin Peaks Lynchian detective that bases their decisions off of dreams, intuition and imaginary conversations with the dead body), and even how failing or succeeding at something can lead to progress in very different ways. If you fail to hit that person you tried to punch, or miss that shot with your gun, or utterly fail to convince someone to help you, you progress through in very different ways so that failing your way to the truth is just as satisfying and entertaining as succeeding your checks to get there.

And of course Fallout: New Vegas. Whether you choose to support the New California Republic, Caesar's Legion, Mr. House, or a truly independent New Vegas, none of them are perfect. Each succeeds in an ideal society in some ways but completely fails at others, leaving you to decide which imperfect system you feel is the right one for the world instead of shoving an obvious answer in your face.

My (new) hope is that in the parallel universe version they didn't do the special edition re-releases and kept in the original Mos Eisley Cantina scene.

Remember friends, Hana shot first!

Spot on. Like he's deliberately trying to be Lil' Gideon from Gravity Falls:

Ah yes, because Alex Garland never makes films that provide a cautionary examination and instead is a complete advocate for bringing those dystopian settings to real life. /s