I need help with flop re-raise sizing and hand ranging on a complete unknown.

2/5, new table, everyone bought at 100 BB. Game is 9 handed, too early to know much about how it's going to play, and about 50/50 people I have played with before/people I haven't.

Stack sizes: there hasn't been any significant action so presume all three players are close to or slightly below 100 BB. Down to 90 at the very lowest.

V1: total unknown, young Asian kid, probably in room because of big tournament running.

V2: Regular, younger Indian guy, moved here for an IT job, lots of history with hero. Clearly thinks a bit about poker but not great. Over-reliant on draws, classically equates hand ranging with wishful thinking ("I put you on AK so I called down 3 streets with bottom pair and hit 2 pair on the river"). Basically, he knows enough to think about what other people have but not much past that, and will make bad odds calls with draws because he can't help himself.

Hero: Too early in this game to establish much table image but V2 knows me to mostly play TAG and frequently ABC because I'd rather exploit weak players than stick myself in fancy play spots. He's also seen me do some stuff outside that box.

Hero in MP with TcTh. Opens for $17 (standard open). Although sometimes this 2/5 game can be sort of limpy/dimpy, until I get the tone of this game I am opening pots I enter for a raise and playing them straight. This plays to both the players I know at the table and the people I don't (who are probably tournament players).

V1 calls, V2 calls. SB and BB fold.
Pot now $58.

Flop comes Td9s6d.

Hero leads for $29.
V1 raises to $70 or $75? (Can't remember exactly, pretty close either way. Let's say $70.)
V2 looks frustrated, shaking his head, looks at me, tanking, then calls.

Pot now $227 ($258 if you include what hero needs to contribute to call raise).

Given that we all bought in for the same amount and not much has happened yet, we're all sitting about the same place stack-wise. Both Vs might be stuck a little bit but no one has less than $375 in front of them. Hero is currently at $450 or so ($413 if you include the call to V1's raise).

Having no information on V1, his raise could mean a lot of things.

I know V2 is not acting. I have enough history with him to know that he has diamonds and desperately wants to hit his flush and is pissed because he doesn't have the price to call and is worried I'm going to come over him.

So, 2 questions:

1) What hands does V1 do this with? I have my thoughts (alluded to below) but I'd rather hear what other people are thinking than lay out my range assessment here.

2) How much do I raise (because obviously I'm never flatting here with top set)? Yes, technically I'm behind some of the time on this flop (to some combo of 78) but I am not reducing anyone's range to exactly that. What's my line?

Some scenarios I considered:
--I shove, which is a huge overbet, but I do so because I feel in the moment that any other raise size that receives 2 calls is essentially pot commitment.

--min-click back makes pot size of $328, which is over 4.5 to 1 for one caller and 5.5 to 1 for V2 if V1 calls. Leaves Hero about $380 behind. If one V calls, pot is $398, if both call $468. Vs will then have somewhere around $320-$370 behind. Do I then stuff any non-diamond turn? I think I have to, possibly check back a board-pairing diamond some of the time.

Side note--if V1 4-bets here, I would still not narrow him to some combo that made the straight and would stuff flop. Flaw in my thinking?

--I raise $199, which is half the pot after my call, and an additional $129 for Vs to call. This is 3 to 1 for one caller and 4 to 1 for the second. For V1 since he is an unknown I can't say if he makes this move with two diamonds blocking V2's fairly obvious draw. If V2 is on Axdd his equity is about 25-27% (30% if it's A7 or A8dd), so with implied odds it's not a terrible call for him either way. This leaves me with $284 and a pot of either $516 or $645. V1 and V2 now pot committed. Again, I'm stuffing any non-diamond turn. I'm also stuffing any diamond that makes my full house because I know at least V2 won't have the discipline to lay down a flush at this depth. At this depth I think I can c/f to a shove if a diamond comes but I hate it.

--I can't see raising anymore than $199 without having to basically shove any turn, diamond or not.

Criticize my thinking here, tell me scenarios I'm not thinking of.

Bonus question: If I'm remembering the hand wrong and I was say, holding the 10d and the board was 10x9d6d does this significantly impact my thought process and my raise options (since it eliminates the board-pairing diamond)?

Flop lead isn't enough on such a wet board. Lead for $40/$45. If V2 is prone it pay it, I might even just bet pot this because I know I'm probably never folding this flop.

On this flop V1 has a range something like QdJd, smaller sets, T9, 87. Other hands that might be in play depending on the players are over pairs, gut shot combo draws like 9d8d, QxJx that isn't a diamond draw, T6/96 and outright bluffs.

I agree that folding this flop is bad. Without history on V1 you can't narrow his range to just straights, and I would assume a tournament player has hands in the second set I mentioned above at least occasionally. Betting small gives your opponents too good of odds unless they are both in diamond draws and block each other. I would generally just go ahead and shove. If your lucky V1 will put you on a draw and call with hands that are crushed. It is a bit of an awkward size but I would want to make a pot sized raise, and is over half of hero's stack so might as well get it all in now. If you think the shove will fold V2 out, then $250 now and shove all turns is OK also. You want to make sure he is getting worse then 4 to 1 but you actually want him to stick around because it puts more money in the pot in the case where you have to boat up to win anyways.

If you did bet smaller and V1 raised I would drop the weaker hands out of his range. I would still give all but the most nitty both straights and sets so folding would be out of the question.

As for the bonus question, it is too remote a possibility to make a difference.

Yes I am never folding to his raise, never flatting. I have second nuts and frankly, a v1 raise with the nuts only makes sense if he wants v2 out, which would be a ridiculously nitty line to take.

So I am more worried about raise sizing because I really feel like anything bigger than 1/2 pot is committing myself and if I do that I'd rather not see a diamond on the turn and shove with my hand strength significantly weakened. But at the same time shoving and forcing everyone out feels like I am losing value. Hence my dilemma.

I realized I left straight flush draws off V1's range. Obviously discounted once V2 comes along but other flush draws are possible group 2 hands also. If V1 is bad you have to include some TX in his range also. Your small bet may have looked like a weak continuation bet and gotten him to raise with a weak hand. If the Td isn't in your hand or on the board AdTd is a possible hand also.

Actually V1 does have to raise here with a decent hand. Your flop bet is so small that V2 is getting straight 4-1 odds after V1 calls so even if he only gets to see one card it's essentially break even. Any implied odds he gets after that is just a bonus.

And yes, betting $250 and then seeing the flush hit on the turn is super annoying. If they both come along you will be getting the odds you need to chase your boat despite the long odds so it's a move in anyways situation. If just V2 comes along and the flush hits you should check/fold, you won't quite be getting the odds and you are very confident he is on the flush draw.

Your lead OTF feels a little small. But, as played, you bet, got raised, and another player flat called. Pot is now about $240 and you have to call $40 or can raise, and you have about $450.
If you raise less than all in, V1 might go all in or fold. V2 is likely to chase.
I'd consider raising $200 more, so making action $270. That's a little less than a PSB, but leaves a barrel for the turn. I don't think shoving here is a bad option either but if you shove, V1 can probably only call with the nuts and V2 is then getting a decent price. That might be ok as you'll need to hit your boat if V1 has the straight but raising less than all in keeps your opponents ranges wider.
Raising less than all in gives V1 room to shove or fold, either of which are fine, and then V2 has to decide whether or not to chase.
The flop lead looked very fishy bc your sizing is so small, which may be why V1 raised, so now V1 might fold to any decent raise and V2 may or may not chase.

The only scenario I care about is if the flush comes on the turn. I want to be getting odds to call a shove. Bet enough so that that's true.

V2's range should be mostly 2p, sets, 78 and combo draws. I'm not reraising to anything less than $300 here given the size of the pot and the odds we're offering to both villains by making it smaller. And since that's such a huge portion of our remaining stack, I just go ahead and shove. Your flop bet is also too small given how wet this board is.

I meant that I see him raising with a decent hand but I don't see him raising with the nuts. Maybe I'm wrong about that.

Agreed with everyone that my bet sizing on this flop is too small. I guess I can't predict what would have happened if I bet closer to 3/4 or pot, but if V1 chooses to click back at me then a shove is a less awkward line to take.

As is I really feel like the raise I make to price V2 out if V1 calls is most of my stack, which is fine since it guarantees I'm priced in to draw to my 10 outs on the turn if V1 is on a straight draw/flush draw.

Oh, and I'll throw out there that at this point in the hand I'm thinking V1 could have as low as a straight draw/flush draw, possible overpair (clicking back against a c-bet) or even some sort of A-pair on the board combo.

Bet bigger on flop, closer to 90% even whole pot, then if they both call, jam all safe turns, if played back at, it is now no longer an awkwardly sized shove

Just ship it. Any diamond, 7 or 8 OTT turns your hand into a bluff catcher, 15 outs to fade and V2 will probably get it in with a ton of combo draws, V1 lower sets, 2p and combos.