Less than half an hour after table started.

Villain 1 UTG [$215] is an unknown mid 30s white male, plain dress, nothing special, plays tight, does limp/fold. Seems to play looser IP, cbets good flops. No showdowns yet.

Villain 2 BU [$300] is 40ish white male, accountant, loose passive all the way. Donks big draws, slowplays monsters. Have some history prior to this day, not really relevant in this hand.

Hero is UTG +1. [covers] Have been consistently raising $8+$2 per limper (experimenting with 'standard' bet sizing), had showdown one hand, raising a bunch of limpers with KJ, hitting a JJ4r flop, checking flop, potting A turn, when overbet/putting all-in a 4 river, got paid by an Ace. Was playing very tight OOP/very loose IP, not sure if Villains notice. This hand Hero is dealt AQ

Villain 1 limps, Hero raises $10, Villain 2 calls, Villain 1 calls.

Flop:
434
Pot:$33
V1 checks.
Hero bets $20.
V2 folds.
V1 calls.

Turn:
4342
Pot:$73
V1 [$185] checks.
Hero bets $45.

I'm putting Villain on 66-TT mostly, and want him to fold.

I think getting an unknown to fold 66-1010 is ambitious unless you've seen he is capable of doing so.

Just give up. They usually station off.

+1 above.... does he seem like the type that thinks, "oh a $10 raise, this is never a big pair! He has AK OR AQ!"

If your impression is that this is a decentish player I'd check it back unless you're willing triple barrel it. You gained more outs with the wheel draw so why not take the free card? overpair isn't folding here often without history.

However, and if you aren't looking for this you should be, how often will this player float/fold what is likely overcards to a low board? I find it has become very common these days even against early position pfr (who a thinking player would assume also has over cards, likely better ones, if not a made hand). Against a player I see doing this I always double barrel heads up.

Lastly, though I know with bluffs its bet the min to get the job done, the round figure of 50 is scarier and can induce scared money to let go if they seem unsure. But yeah, I'm mostly checking it back here.

Bad spot to double barrel. Nothing he is going to call the flop with is going to fold on this turn card because it isn't scary in any way. You want to double barrel on cards that scare them, like an overcard or a 4 flush or 4 straight.

I'm usually fine with a double barrel here but with no info on villian I think I check back turn and maybe barrel river if a picture rolls off. Don't like burning money against a villian I'm not sure is capable of folding here with a small pp.

If you're double barreling here you're gonna have to ship the river and hope he folds his overpair. Id pick a better spot if I were you