Played this hand recently and have gotten different responses from people on a couple different streets so looking for more input.

Background: H is young 20s white kid, TAG image. Putting money in the pot but showing good hands in general. Maybe image of being a little snug recently as I've lost a couple bigish pots and am now a little short at about ~$170.

V is LAG persian guy in mid 30s. Chatty. Seems to be thinking player but plays too loose for his own good with VPIP around 50%. Very wide range IP. Aggressive pre and post. When I sat down he had over $500 but had been losing recently and was down to ~$200

notable history between us:

hand 1: I raise button to $12 after one limper with AKo, he flats in blinds. I say "damn man, leave me alone" since he had called my last 3-4 raises. He checks dark and flop comes A62r. I check back hoping to induce. Turn T complete rainbow, I call $15, River Q I call $50 and I'm good

hand 2: I raise 44 to $10 from HJ and V 3bets me to $20 otb. This is the second time he did this against me IP and third overall in the span of an hour and a half. I 4bet to $50 and he thinks for 30s and shoves. I fold and he shows KK.

hand 3: V raises UTG to $12, one fishy caller and I squeeze with AKo in SB to $40 hand after losing a $250 pot. V calls, other player folds. JJ4r flop goes check/check, 8 I check/call $5, Q river I c/f after he bets $40

otth
After playing pretty snug for an orbit or two I raise AdTd to $12 in HJ after one limper. V calls and rest fold.

Flop ($24): 5dJc9c
H bets $15, V calls pretty quickly

Turn (~$50 after rake): 8h
H think for 10s and bets $35, V thinks for ~30s, asks to see my stack (he did this pretty often), thinks another 30s and calls.

River (~$120):5h
H thinks for 15s and shoves for $108, V...

Thoughts on flop: an over and two backdoor draws with the chance to barrel any diamond, K,Q,A, or 8 was what got me to bet but some people I've talked to have argued against this V they'd rather just c/f OOP. I could see either being ok, curious what you guys have to say.

Turn: I didn't bet this flop with the plan of not continuing on this turn so we follow through and set up a good SPR for river.

River: I know that this is not the best river for me to bluff on but from what I had seen, V tended to raise his strong hands on wet boards before the river and didn't slow play often. In game my thought process was he has so many one pair + draw or Jx hands on the turn that have a tough time finding calls otr when I jam here since he's so wide otb pre. Then again I don't rep a ton of value hands (QQ+, boats, straights and strong two pairs).

So what do you all think?

The river shove is probably the best played street. The flop is better as a x/f, same ott if it checks through.

Jc 9c 5d smacks calling ranges.

I would take that line occasionally but not often. In this sort of situation you need to give up flop or turn a fair portion of the time. On the river you have represented AJ or better the whole way so at that point I probably shove most of the time.

How often I give up depends on how likely villain is too station with a pair+draw.