This was an episode with a lot of feels, mostly about Dean. And I think that they're ripe for interpretation in a lot of different ways, especially if you're coming into it with strong feelings about one character or another. Well, my strong feelings are love and hugs, so read below for character discussion tainted by niceness (it's so hard to get out in the wash).
So here's what I got from Bad Boys that I am sure someone on Tumblr is disagreeing with entirely right now (which is why this is here and not there): Sam, who ran away from home (initially I wrote Dean...) and got a dog that Dean didn't learn about until recently is so reflexive about his immersion into his brother's life that he doesn't countenance for a moment that anyone calls Dean a nickname that he he wouldn't know. I guess he doesn't know how much he doesn't know, because he has a bit of a habit of being surprised by things Dean does—what he reads, engineers, who he falls in love with...ah, Sammy. You're getting there.
Top that off with the lying about the arrest and petty incarceration Sam's starting this episode on unsure footing. The cake is a lie.
It could have been a Something Wicked type of situation where the normal distractions pulling on a teenaged boy overrode his mandate to parent Sam and he just wanted to play poker. Maybe there's something he wanted to buy that he couldn't afford—either for him or Sam. Maybe it wasn't going to be enough money for some reason—poor planning, hunt took too long. *I* don't blame John for that happening (carelessly leaving them with too little money, drinking through the grocery money, etc), and I don't blame Dean. Shit happens. And Dean probably tried to make it better with the tools he had to hand. Fanon alert: If this show ever hinted at him tricking for money as a teenager I will throw up in my mouth a little. That's for fanfic alone, thanks. Canon's bleak enough as it is.
Hustling cards failed, stealing failed. So John leaves him. Is John mad? Does John think a dose of juvie or whatever punishment he's going to get will do a boy good? With his former Marine and current drill sergeant mode of thinking, this is the conclusion that I come to. He's not going to be overly sentimental about an absence of two weeks, and he trusts Dean to be on the job and protect himself (as he did, dutifully, warding the beds) and hopefully learn a lesson. I'd assume they don't want to tell Sam Dean was stealing, and shortly afterwards, they don't want to give Sam ideas.
Oh, and the bruises were from a werewolf. I don't want to hear about John abusing him. That well is dry, and it is a mirage.
Dean's not seeing himself in Timmy, as far as we've been shown. Is he seeing Sam? I don't think so, although Sammy was bookish, he seems to have been a loner by choice and hung out with kids that needed people on their side in After School Special. So that's just Dean and magic facility with kids. I like that they still play this, and the running leap into Dean's arms at the end made my heartstrings clench. But I don't think that despite plot similarities to a story of our own, that Timmy is echoing either brother's journey.
Flashback moment of note: Dean's sixteen, he's with a girl who plays the guitar, and he wants to get away from the family business and be a rockstar. At no point do we see him express any interest in or talent at this or any instrument, and the instances we've seen of his singing have been deliberately bad.
So here I'm seeing the kid who loves his father's records and the rock and roll life here, not someone who's looking to turn either love of or talent at music into a great career. Some kids want to be astronauts, some want to be archeologists, Dean does not want to need to finish high school for his, clearly. He segues into a mechanic here, his father's previous occupation, so even as he wants to give up the family business, his choices are "completely impossible" and "the other family business."
I think right there we're not supposed to feel sad that a dream passed him by, at a profession his father's mission and militant protectiveness prevented him from having. I think we're to see that he still could dream—that he had boyish impractical desires and was tempted to do boyish impractical things to make them come true. John had not drummed childhood out of him, either by mistake or on purpose. The audience is the grownup in this scene, not fellow adults who regret giving up on their dreams too.
This is reinforced, IMO, by the conversation with the adult Robin, where she reveals that the dreams she had at 16 weren't really her either—that where she is right now, doing both her father's job and her mother's is the right place for her to be, and the right things to do. Is it deliberate that she's working at both her parents' professions? Is this saying something to Dean about both hunting and being a Man of Letters? Certainly, though, the parallel of we're doing the right things now is spelt out here.
At age 16, it's the love of Sammy that takes him back on the hunt with some regret, but without ambivalence, IMO. It wasn't about family, it was Sammy. But ten years later, when the series starts, it was about family. Once he'd gotten Sammy, he needed his father back as well. That's what adulthood had taught him was important to protect.
At the very end we're shown a mother who loves her son so much she stays around to protect her son, but she's been driven mad by the trauma of dying. Mary stuck around in similar circumstances—but we see, in Home, that it takes saving Sam once for her to release and leave with an apology. This mother shows no sign of Mary's gentleness and decision-making—like Efraim last week she has no sense of proportion—she can't tell what threat deserves what level of punishment or deterrent. What made Mary different from Timmy's mother? They're both horrific deaths with young children barely saved...I can't suggest much. Maybe knowing about what makes a bad ghost helped her not go all Shining on anyone, and just step in when Sam needed her the most, and then disappear.
That's two really sad character study episodes in a row. And this one with way less comic relief. What are they doing to us? Are we being tenderised?