players:
Hero: I've ran like god for an hour stack went from $200 to $500.

Main villain (v1): had huge stack when I sat down, has like $700 now. He loves to straddle and make overly large bet/raises. will fold to counter aggression.

2nd villian. solid. seems frustrated with v1 and not getting good cards. has like $250ish?

v1 straddles to $4, v2 and another call. Hero is on butt on with KQs. I think about raising , but v1 has shown reraises twice when his straddle is raised, plus he often raises straddle. I figure I will call and probably call a raise from him. surpisingly he checks and we go 5 to flop.

FLOP: A 9 3 ca ching!
v2 bets 25. seems an obvious call here hoping v1 comes along.
V1 raises to 100. all else fold. I think a while (hoping to not like it, also debating reraising here). I finally decide to float it and hope to raise on non-paired turn. will have to evaluate if it is a paired.

Turn: T ... hmmm. that's a crappy card. unless maybe he has the jack. v1 checks, I decide to check, rep. a big hand that doesn't like the spade. My thinking here is , he folds anything except a big spade. the only thing i can do is pretend i don't like the spade either?

river.. another low .. a 2 I think? he checks...

Hero does ?

Seems like villain just tried to take down the pot OTF with a nice raise, then once you called he gave up.

e: I make a smallish bet like 60$ here and hope to get called by a smaller flush.

Reraise flop here all day man. You lost sooo much value from hands that would have put more money in until the 4th spade smacks the turn. When v1 over bets the flop and then v2 still raises it up, there is no reason to slow play. you have multiple villains showing great interest in a hand where you have the nuts. time to get the money in and quick.

What has villain 3betted his straddle with the other two times? Anyhoo, I'm raising first time around preflop. I think I'd rather have the initiative postflop, especially since we'll be in position (i.e. cbet, take it down with K high, buy a hot dog, next hand).

I raise the flop. I don't think our whole strategy in this 5way pot should revolve around V1 who could easily be check/folding this flop. I raise now before a scare card kills our action. As played, I guess I'm cool with flatting V1 since we'll be in position on the turn and we'll be able to get rest of stacks in if we choose; we're still risking scare cards though.

Crappy turn card. I doubt villain has the J, unless he flopped the J high flush. So it looks like he's either completely bluffing on the flop or he has a real hand like two pair or a set or something. A bluffing hand would probably give up to a bet but might bluff the river, so I guess checking is better in this case. A real hand (especially a set) might pay off a bet, so betting might be better. All in all though, we're playing kinda deepish, so I'd err on the side of making sure I don't horribly slowplay this hand to a big loss (which a river pairing board might do), so I probably bet out upwards of 1/2 pot.

As played (especially showing weakness on the turn), I'd probably just shove the river and hope he levels himself into a call with some dinky spade or fools himself into thinking we're probably chopping with the flush on board.

GcluelessNLnoobG

Being this deep against a bad villian I think we need to find a way to just get more money in (and hopefully our whole stack) instead of being tricky and trying to maximize value against bluffs. I would raise somewhere on the flop, and given action bet the turn (probably small, 1/2 pot so, encourage a possible spaz.)

well, i was all set to bet turn on a non-spade. I kinda froze and ended up checking, i think a small bet was in order. as was, i bet wayyyy to big on river ($150). and he folded.

I'm with you until the flop based on the reads you give.
Floating here is not something I'm doing for 1 main reason your hand is never going to be one that hates a 4th spade, you either had it already or got there with the 4th spade and I will shut down until you show me otherwise if i am villain.
For this reason the check on the turn is also bad; your not repping anything but the nuts like 90% of the time here.

When this flop comes and an extra $125 is in the middle already just re-raise and be happy with whatever happens, you've got tons of value already staring you in the face and as a bonus; in my experience its not that uncommon at $200nl to see people just lose their minds for no reason and pay you regardless.

This is what I told my friend if the guy has set or two pair and you flat the 100 dollar raise you risk letting board pair for free . Also you risk the 4th spade coming out totally ruining your hand! If you reraise here you can get more value or take down an already big pot without risk of board pairing!

FWIW, I probably would have bet on the turn for value. And the suggestion of others calling for a Hero raise OTF with 2 villians overbetting has merit.

OTR, my first reaction was to overbet. After reviewing the board, the problem is OTR Hero doesn't have the nuts any more. If V1 has two small spades he just hit wheel SF. If V would make that big flop raise with a small made flush his betting might fit the idea, if R was indeed 2s, that he might have 54ss. If he's a thinking villain, I don't think he's going to call OTR with a set/2pr or a small spade flush on this board because he probably would read Hero for spades with the call OTF. The only hand we're beating I think he might call with is something with the Js in it. As an overbetter/folder to counter aggression he might not. All in all, if I thought V1 was capable of fast playing a small flush OTF and knowing he overbets and folds to counter aggression, I'm thinking he'd mostly fold to any bet OTR unless he has H beat. Conservative me thinks I'd check behind OTR.

i do believe it was a 2, because there was a SF possible. Yeah, i def. remember thinking that on the river. i still went with the largish bet. if he shoves, maybe i can get away for my last $300. I thought not betting there was "monsters under the bed" syndrome. My only thoughts were about sizing.

In retrospect, I'm leaning toward reraising the flop. if he has a big hand like smaller flush or set, I can still extract value. if he has less, hes not paying more on later streets.

also, thanks for the input. I don't think, in general, I'm good at extracting the maximum from big hands.