Just got back from a Sunday morning session and this hand stuck out to me as one that I misplayed. I'll give my thoughts/reasoning at the end.

Hero[$300]: Mid 30s White Guy. Been sitting for about 45 minutes or so and playing very snug so far. This is the first hand i've raised. Haven't played any other hands that weren't free from the BB. Nobody has commented on this fact.

V1[$200]: Younger black guy. Has gone through two buy ins since i've been sitting. I don't think i've seen him fold for a single raise pre flop so far. He's been calling down with all draws and as low as 3rd pair.

V2[$190]: MAWG. limp/calls quite often. Mostly playing pretty passively although I've seen him donk a multiway flop with a OESD as well as middle pair to "see where he's at".

V1 Straddles UTG for $4, folds to V2 in MP who calls, folds to H in CO who bumps to $17 with J9, blinds fold, V1 calls in straddle as does V2.

Pot[$54]
Flop: 863
V1 checks, V2 bets $25, Hero calls, V1 folds

Pot[$104]
Turn: 863J
V2 bets $25, Hero raises to $70, V2 calls

Pot[$244]
River: 8634
V2 Shoves for $78, Hero Calls

So as i mentioned above and in the title, I think I misplayed this hand by raising the wrong street.

Raising the flop does a couple things:
1) V can fold better
2) Can possibly give me the option to take a free card on the turn
3) Gets money in before a hits which could shut down V's aggression
4) Balances my flop raising range a bit as i'm undoubtedly seen as tight by other players. I'm playing face up if I'm only raising the nuts on the flop. I don't give a lot of weight to this one as very few Vs pay that much attention.

Any thoughts on both the line I took and also my thoughts on the alternate line?

Considering the straddle, you're 50bb effective. I'm dumping this hand pre always since I know we're getting called by V1 and sounds like we can't bluff him post flop much.

Anyways, we flopped decent. 2 overs + FD but far from the NFD. Calling the flop isn't an error since you're getting the right odds. Raising is ok too b/c we have a ton of equity if we're around for the river, but as mentioned, someone could have a higher club draw. I think the largest mistake was isoing the limper pre.

I agree that preflop is the mistake in this hand. With the straddle in play you are not deep enough to flat and your hand isn't strong enough to raise a station with short effective stacks.

After that you got too good of a flop to give up. With position, 2 over cards and the flush draws calling flop is best. It's better to flat call and let V1 come along with his single pairs and weak draws anyways. After that your top pair+flush draw leaves you committed against a villain that isn't deep. It's just a question of getting it in on the turn or river.

Point taken on pre flop. I was a little impatient yesterday as a whole since I hadn't played in a while and this is probably a good example of it.

That being said, I'm still curious why calling flop his the optimal play versus raising. Is V1 the deciding factor in that decision? Calling flop gives V1 a chance to draw with correct odds with flushes and a lot of straights, no? If he's going to call regardless, I want him to make the play that's the biggest mistake which is to call without sufficient odds (folding, per my read, is unlikely).

I feel like raising the flop sets me up a little better for turn and river play as:
1) Depending on the turn card, a second donk into me looks really strong and lets me dump my hand easier when a bad card hits.
2) Gives me the possibility of a free card on the turn, when this option might not be available had I given up initiative on the flop.
3) Disguises my flush a bit when I do hit it.

I just don't like bloating the pot on the flop with a J high flush draw. I can see why you'd bet, and I don't think it's an awful play or anything, but I'd rather just control the size of the pot, and then bet for value if/when you get there. I like the line you took.

Limping the $4 in position can't be too bad unless V1 is likely to raise his straddle.

I think flatting the flop is fine. Unless V1 floats with like AJ/KJ/QJ you are happy to have him along for the ride. He's a station so he's not going to fold his strong draws or decent pairs anyway but even most stations know to dump their trash facing a cold raise. His range is so wide, no need to narrow it when you have a good draw.

There are a lot of good turns for you and a lot of scary turns that might cause the action to check to you for you to take a free card or bluff at.

You could make a case for shoving the turn, I think... His bet is really small so your raise just gave him 5.4:1 to call. If he has a lower FD that's fine but if he has a bigger draw, straight draw, or one pair you are giving him way too good of a price. A bigger raise than $70 surpasses half of V2s stack so may as well shove and see if he will make a bad call for 2.25:1 or if he's somehow ahead you have a healthy amount of outs.