Last night table 2/5 table has a max 60bb buy in and the stacks are pretty deep for this game. Hero has about 200bb and has tabel covered average stack is about 120bb.

Hero in mid position with pocket 5's two limpers I make it 25 to go. Folds around to the initial limper who is an older white man who I say has a decent tabel image but not nitty. Plays his hands mostly ABC but check calls way to much IMO. Limp folds often so really easy to exploit. He has about 150bb. Second limper is an agro idiot who will jam over the top on any flush draw with out exception. Blackjack style get it in at all costs person. He has 75bb or so.

Both call.

Flop comes Jd 5h 2d

OWM leads for 60, agro-idiot folds. I raise to 160 OWM tank calls.

Turn brings 4d OWM checks and I just do not put him on a diamond draw here. When he leads the flop here I put him on AJ or better. I bet 275 and he snap calls.

Now I don't like my hand much, in my mind aside from solidifying my range for him in the hand I am now trying to evaluate his image of me. What could he put me on here does he think I am taking this line with an over pair with a redraw to the nut? Is his hand so big that my hand doesn't matter?

I tell myself if he leads river on the flush and straight board am I suppose to call here? Do I check behind if he doesn't? Do I bet fold here?

Put the last 290 in on any non diamond river. After the turn his most likely holding is prob AdJx. I agree its unlikely he has you beaten now.

If his image of you is lagging I think we need to get value from our hand on a good river ie non diamond / straight card.
I hate these spots and will sometimes check back but I think this is super bad.
If he leads I'm looking for body language tells for my decision.

These are the spots for me where I feel I am loosing value, but I hate bet folding these hands more than loosing value.

This is a leak I know I need to plug.

You have 290 left in a pot of over 800, your only bet left is all in. b/f with that little left is no good

I've got the pot at 75+320+550= 945 here. ~ 290 left to play for. Not enough chips remaining to bet / fold anything IMO. If you misread his stack, and you have ~ 500 left to play for, I still don't think bet/fold is a good option.

I ship it on any non diamond... and I'm hoping for an A or J to hit since I can't see how he could fold either of those cards given your read and this action.

Grunch

You need to tell us what the river card is if you want advice whether to bet it or not. Also, bet less OTT. Why bomb the turn? Are you trying to get him to fold bottom set? The pot is... ~$395, I probably bet slightly over $200 maybe less (in retrospect $275 isn't all that much, but yeah I still go a bit smaller since his range is likely one pair or a flush).

Assuming that the river is a brick and he checks... he's only got $315 left? Go all-in.

River was a black Q, and he ships it,

Hero?

Hero throws up in his mouth and probably cry calls knowing V takes this line with a flush almost every time. I think the problem in this hand is your flop sizing. Raising to 220 puts him to a decision on the flop and usually gets him to either shove or fold his flush draws instead of calling and putting you to the tough decision when the flush hits on turn. If he flats 220 you can shove all non diamond turns for a PSB and he can't really have just a flush draw calling that size bet so his range would be weighted more towards 22/AJ/QQ+

Yeah this sizing is much better +EV