#5.08

"But I'm not... a kid anymore. And I'm not Sara."

anyway. the thing about john is that both the angels AND the demons wanted him to be doing all of that. they wanted him training and ruining his children. they wanted sam to be sharp and angry and resentful and they wanted dean to be hollow and broken and order following. (hell, chuck wanted it too.)

like in 2.21 azazel says this to sam:

AZAZEL: You’re tough. You’re smart. You’re well-trained, thanks to your daddy. Sam – Sammy – you’re my favorite.

throughout season 4, we see that the angels are testing dean specifically on how good he is at following orders - especially ones he doesn't understand or agree with (4.03, 4.07, 4.10, 4.15, 4.16, 4.17, 4.21, 4.22). summarized here (4.07):

CASTIEL: Tell me something, Dean, when your father gave you an order, didn’t you obey?

5.08 lays out the angels' vision for dean and sam's desired personalities from their upbringing:

GABRIEL: Why do you think you two are the vessels? Think about it. Michael, the big brother, loyal to an absent father, and Lucifer, the little brother, rebellious of Daddy's plan. 

so john could have moved his kids one town over in kansas and let them grow up and play sports and go to school dances and become a lawyer and a firefighter and that would have been more contrary to the schemes of all the sinister forces working around him than every single thing he did.

his kids didn't need to learn to hunt the supernatural. (besides the extra-canonical stuff in the john's journal book) nothing actually attacks or tries to harm his kids* until sam is twenty-two. (and the angels only come for dean after he DIES)

in fact, in 5.22, we learn that lucifer and azazel had sam surrounded by demons for most of his childhood** and no matter how prepared john felt he was and how protective of his family he thought he was being, he never caught on.

5.22

LUCIFER: Look closely. None of these little devils look familiar to you? SAM: That's Mr. Bensman... One of my grade-school teachers. LUCIFER: And that's your friend Doug from that time in East Lansing. And Rachel... your prom date. Sam Winchester, this is your life. Azazel's gang – watching you since you were a rugrat, jerking you around like a dog on a leash.

brady is actually the only demon we know of from sam's circle from after he leaves john.

5.20

BRADY: Brady hasn't been Brady in years. Not since, oh... middle of our sophomore year? SAM: What? BRADY: That's right. You had a devil on your shoulder even back then.

but the demons from sam's childhood don't actually seem to have been doing anything beyond watching to make sure sam stayed tough, sharp, smart, well-trained, etc. like brady only steps in and kills jess because,

5.20

BRADY: No, we could tell we were starting to lose you. You were becoming a mild-mannered, worthless sack of piss. Now, come on. We couldn't have that. You were our favorite. So I hooked you up with a pure, sweet, innocent piece of tail. And then I toasted her on the ceiling. 

2.21

AZAZEL: I mean, sweet little Jessica – she just had to die. You were all set to marry that little blonde thing, become a tax lawyer with two kids, a beer gut, and a little McMansion in the suburbs. I needed you sharp, on the road, honing your skills. Your gifts.

so, yeah, maybe there's a version where john tries to give them a normal life and the demons (or angels) intervene. but the version we have is the one where john was so hell bent, they never even got a chance. he played right into the demons' and the angels' plan.

the version we have is the one where john chose to have his son be bait (1.18, 1.20, 15.16), and shoot at gun at 6 (2.06) and leave him alone with one at 11 (1.18), and get enough of a criminal record to make any normal future at the very least humiliating, expensive, and deeply bureaucratically challenging. the version we have is the one where the most consistently harmful and damaging presence in his kids was not the supernatural but himself.

hell, the whole apocalypse plan in its entirety could be been thwarted by john teaching dean that his life mattered in and of itself and that his worth wasn't only found in making sure sam was ok.

the most powerful resistance to the schemes of the angels and demons, would have been john giving his sons a safe, stable, loving childhood.

*except you know all the monsters that attacked them on hunts john made them go on.

But then, on Tim's side, I immediately think of their second first date... with the same ambiance... and I just love this...