I'm enjoying this fiction a lot; hope you don't mind but I have a couple of suggestions for the sake of realism.
A 1967 Chevy Impala doesn't have a check engine light (unless Dean installed an engine computer and a modern dashboard). He'd realise something was wrong when the engine note changed or the steering started pulling.
Gasoline is transparent, lubricating oil is translucent yellow when clean, black or brown when dirty. It's transmission fluid that is red or pink. A broken exhaust line or shattered suspension coil again would be the most likely result of driving through the woods and again Dean would most likely notice very quickly. Oh God, oh Castiel it's true what they accuse me of. I AM a petrol head!

Poor poor Baby. Poor Sam's wallet.

Loving it. Please keep destroying The Black Dog

typical teenagers, realistic scenario, intense, good rule to follow, nice that John showed up and was so caring to Sam,

scary and sad story, well done

Aside from drinking, Dean really didn't do anything wrong. :(
Anyway, impressive how Dean could stop and break down the situation step by step that way.
Rule: Don't feed after midnight lol

Poor Dean. All he did was allow Sam to tag along. Most teens wouldn’t have. The drinking, ok bad idea. But for the rest, Dean handled it very well. John is being an ass, as usual.
Rule: Trust your gut, not logic.

I just gotta say, YOU FORGOT THE 2 MOST IMPORTANT RULES OF ALL, 1 YOU CAN'T SAVE EVERYONE, 2 DRIVER PICKS THE MUSIC, SHOTGUN SHUTS HIS CAKEHOLE

Good one. Having John, be the one, who makes the near fatal mistake, for a change.

I wonder if, in Real Life, Somebody has actually died because of the”Cinnamon Challenge”?

A shotgun, to replace a table leg? Not the smartest idea. Or the safest.

Chupracupa Puppies?! I’ve only got one word: Yikes!

After reading this, I just thought of another rule: Beware of Teenage Girls(and the darkness in their hearts).

I 3 Rule #11.

Yep. Definitely put the phone on airplane mode, while hunting. But another phone-related rule, would be “Always keep your phone charged.”

Loved the chappie! It was awesome! Please write more when you can.

These are amazing!

Also, I'd like to suggest a prompt. "Don't fight/argue during a hunt."