Game is 1/1/2. Minimum open to $4, and there's also a "kill" button in play that can be bought for $4 from any position except the button, changing the stakes to $8 min bring in, and the kill acts after the BB PF.

Reads:
Hero: 30ish TAG. Has shown 2 hands in last 3 hours: AQss that got all in with a shortstack on an A35 flop, and AA for an open raise that got no callers. Hero has raised/3bet and Cbet around 4 hands in the last 60 minutes, winning them all.
Villain 1: Japanese guy in mid/late 40s, but could be 60 (they age so damn well!). His play has appeared pretty competent. I have only seen one of his hands where he turned broadway, but he's not in a lot of pots, and he's fairly aggressive when he is in one. Villain has only been in one hand with Hero - one of the aforementioned raise/cbet hands. Flop was KJx and V1 asked me if I had AK after he folded. I said yes (it was actually QJss), and V1 said "I knew it! I folded KQ". "Good fold." So my image is fairly rockey in his mind.

V2: Asian lady in her 40s. Will play any hand if it "feels lucky" and has already blown through $500 in the last 5 hours I've been at the table.

Stacks:
V1: $340
V2: $140
Hero: $290

Pot is a kill pot, so minimum bet is $8, and there's an additional $4 blind out there.
V2 (MP) opens to $9.
Hero (Button) 3bet TT to $29
V1 (BB) calls.
Folds to v2 who calls.

Flop ($89): 8T4

V1: check
V2: check
Hero: check

Turn ($89): 8
V1: leads for $50
V2: fold
Hero tanks for 20 seconds and calls.

River ($189) 2

V1: leads for $15
Hero raises to ??

I'm trying to figure out what the right raise is here. I figure the range for V1 that I can get any value from is any two diamonds J+, 99, JJ, QQ, or suited connector that includes an 8. That ultra tiny river bet baffles me, though. I don't know if he's trying to get a small amount of value with the nut flush, or if this is some sort of ill-conceived blocker bet.

You need to bet the flop, that's the root of getting the maximum.

AP, ignore the $15 and bet whatever you would for value, somewhere in [100,130]. I expect him to have nothing a lot of the time. I make this tiny bet when I feel it'd be easy for V to rep a made hand if I check and I have a hand that I just can;t call with. Often it's a set on a board that's run out 7-8-9-T, they just don't raise without it, they'll flat a tiny bet with 2 pair or even a better set, you at least get to showdown.

I'm also 3betting preflop as our stacks are very small with the kill on against V2, plus she's gambooley enough where we'll be quite happy to get her stack in preflop here.

Pretty sure I don't like the flop check. Board is drawy (flush and straight draws) so let's charge for those draws with our monster and before a scare card comes to perhaps shut things down on the turn (also realizing that any overcard could also be a scare card for opponents). Stacks and position are small enough where we could slowplay, but I just don't think this is quite the board to do it, imo.

I don't hate the flat on the turn. We'll have about a ~PSB left where we can still shove the river. But we still risk a scare card coming that could shut this guy down. Meh?

The only bet on the river is an all-in as we only have a ~PSB left. Unfortunately a scare card hit, but that was the risk. This guy has already folded a big hand to us, my guess is that eventually he might be getting tired of that. Note that he might also figure out that we didn't cbet the flop, so it might seem less likely that we had a flush draw. Shove is the only bet size, imo.

GcluelessNLnoobG

Well OPs hand loooks alot like a flush to me but...
Bet flop
Flat turn
Now just bet like 100-125 ish and hope he has an 8 and/ or shoves over top

A naked 8 is never shoving over top of a raise on this board (they will either call or hero fold).

However, a naked 8 might call a big bet, and there probably isn't a whole heckuva lotta difference (if any) between them calling a big bet vs a shove.

Gshippittydoodah,nothingelseisclose,imoG

Flop check is bad.

Turn flat is really bad.

As played inform the dealer you were supposed to be all in awhile ago and therefore you'd like to go all in now to make up for your mistake.

JFC please bet pot on this flop.

As played, raise turn to $115.

As played, raise river to $200

You really need to be betting flop or raising turn here. You have a monster hand but you need the pot to be bigger for a river shove to be a reasonable bet size.

The big turn bet and small river bet looks more like a small blocking bet way more then a silly small value bet. Shoving over that would be a pot sized bet, and is going to fold all but the monster hands unless villain thinks your bluffing. As played, I would go $100 on river. I'm targeting flushes and 8X hands here. If your lucky he has a big flush or a boat and will raise you, but if his hand is that strong it doesn't really matter what you bet all the money is going in.

He's not calling anything more than a min raise (and that's just out of curiosity). A tricky player will make an insult bet here with a boat, but this guy isn't tricky, he's pretty straight forward.

His bet is a feeler "to see where he's at" with some type of marginal hand.

Your best option is to shove and hope he accidentally knocks one of his stacks into the pot with his elbow upon recoil.