Background: First hand at the table I raise QQ to $12 UTG and get flatted 4 ways, BB shoves $129, I re-shove, folds around and I lose to his KK. Few other ridiculous spots and I'm in for $500 and not loading up anymore. I'm not visibly pissed off but internally I'm pissed off and probably playing my C+ game. This hand is about 2 hours later.

Villain was not at the table for too long - he's mid 20's nothing special pretty much a rec-fish ($150). Limp folds a lot, isn't raising much. We're down to 5 handed this hand because 2 people have left the table for smoke breaks.

Hero has $83.

Folds to hero OTB and I make it $8 with K9o. If I steal blinds, fine. If he calls, fine. I'll gladly play this hand in position with initiative.

Flop ($17): A68
Pretty good flop for my perceived range, can easily rep an ace. V checks and I actually only have 3 green chips left so I toss one in and overbet the pot to $25. V thinks 10 seconds and calls. OK, maybe he has a 6, 8 or unlikely an Ace - I think he would have bet out with an ace. If I pick up a K or 9 on the turn I'm pretty confident I'll have the best hand.

Turn ($67): 2
V checks. I like the fact that he checked however we're quickly losing all showdown equity and probably only have fold equity left. We have 2 green chips left ($50).

What do?

He would have to peel the flop super light for you to have any fold equity. If he limp/folds a lot then he knows how to fold. Save your $50 and give this up. Its way too easy for him to call with you being all in. If you hade $300 behind a $50 bluff may scare him off a weak A, but not here. Your K high beats a lot of the stuff a turn bet would make him fold anyways.

I check. V never folding an ace, esp with the flop overbet.

If you had made a better bet on the flop then barreling could be an option, although unlikely, but I don't think you have much fe so I'd check it back and try to get to showdown and hope K high is good

Hero shoves his last $50 on the turn hoping to rep a strong Ace to get villain to fold all pairs (except A).
Villain thinks for half a minute.
Hero thinks 'fold, fold, fold'
Villain says, "50? I call".

River bricks out and hero stands up to leave. Agree with the consensus that once called we should typically give up. Trying to barrel people off hands when you aren't deep and they aren't even thinking about your hand at all just isn't profitable at $1/2.

Your risk/reward ratio is way out of whack trying to make blind steals at 1/2.

I don't like the overbet OTF, 2/3 should suffice, you are risking less. As played I am giving up and checking OTT, I don't think there is much villain can be calling once then folding OTT.

Fold pre. Check flop.

As played check the turn. I don't think that you're getting anything to fold here. Check and hope for a K.