This hand happened several months ago at the Borgata, but I still think about it now and then, so I thought I'd put it here.

V1, MP, 600 - Youngish black dude, capable of bluffing in small pots, but straightforward when the bets get big. He's clearly thinking about what's going on, but he still does a lot of fishy things and doesn't have a great understanding of relative hand strength.

V2, button, 120 - Pretty aggressive for a 1/2 player.

Hero, BB, covers -- I've been playing a lot of hands and running well. I stacked "PROFESSIONAL!" (for those who play at the Borgata) in a pretty thin spot just a few orbits earlier for 150 bigs, after which I loudly yelled "professional!" (obv), so I am probably perceived as a young rich fish who's there to have fun. He had doubled through me exactly one hand earlier and yelled "professional!" so this is slightly less douchey than it sounds.

V1 limps, V2 limps, sb folds, I check in the BB with 86o (no heart).
Flop (7): 754hh

I lead for 15, V1 raises to 40, V2 jams for 115.

I think the tough part of this hand is that I only rep made hands if I raise because the short stack is all in, but there are clear drawbacks to calling too. Thoughts on how to proceed?

$205

Raise and shove all turns.

I know PROFESSIONAL. He's fun to play with and actually a nice guy who loves to gamble and consistently loses. Whe he wins a hand and yells PROFESSIONAL, it's hilarious, unless it's against you.
On this hand, you flop the nuts with no redraw. You bet, got raised and then another player shoved all in. I'd jam. I'd expect to get called by hands like A6hh, 76, 75, all sets, etc. we're way ahead, but won't like it if a heart hits or the board pairs. It's a limped pot, and it already has 80bb+. If we jam and get called, great. If all fold, that's ok, too. A small raise might get more folds than a shove here so I'd opt for the bigger play.

All in jamboree

well at i'd actually just raise but - try to GII

You absolutely have to raise here. Only question is whether you're raising all-in or raising to $200-300 and jamming the turn.

Keep in mind just how much of the deck is, in one way or another, bad for you:

-9 hearts complete a flush draw.
-6 non-hearts that pair the board.
-7 non-heart 8s, 6s, and 3s put a four-card straight out there.

15 of those cards are bad news for you. Another 7 will kill your action. That's nearly half the deck!

The additional problem is that, since you'll be out of position on the turn, you really don't want to check-evaluate if a heart or board pair shows up. Doing so let's him decide between bluffing and taking a free card.

So I think this is a spot where you should raise enough on the flop to commit yourself on all turns. Raise to $300. If he calls, you auto-jam the turn and live with the results.

You had me at "doesn't have a great understanding of relative hand strenght"

raise to $296, shove turn

I ended up jamming since I thought it was pretty clear that I would hold an equally strong range of hands regardless of my sizing and villain either had a hand he was going to the felt with or that he was folding for 200 or a draw that has at least decent equity against me. He ended up thinking for about a minute, and then folding. The all in player had top two and didn't suck out.

I think the smaller raise size would have been a better play because it probably looked stronger to make a 600 dollar bet than it would have looked to make a 250 dollar bet even if both plays were in actuality equally strong.

The only thing I would add is that your perception of V1 as fishy and relatively not understanding hand strength works against you this time.

If you raise to $225-$300, a smart player might think you are trying to isolate the all in, prevent callers and call just a hair lighter.

But with the gentlemen, from your explanation, I feel like he might just see every bet as over $150 as strong regarless of the context of the situation.

So I am not sure if your smaller bet would have received a call against this V.

Did he say what he had/folded?