Did I extract enough???

I wanted to extract as much of the money as I could in this play. I thought about going all in but his bet on the river showed weakness so I thought betting the pot size was more productive. Should I have dropped the hammer??

***** Hand History for Game 3153292985 *****
0/0 Texas Hold'em Game Table (NL) - Tue Dec 06 02:39:11 EST 2005
Table Table 69915 (Real Money) -- Seat 5 is the button
Total number of players : 10
Seat 1: RenatoGomes ( $26.70)
Seat 2: JustMutt ( $22.71)
Seat 3: ace_white ( $21.65)
Seat 4: s1Lv1a ( $24.80)
Seat 5: KINE_STUFFS ( $28.75)
Seat 6: Pistachio79 ( $80.05)
Seat 7: BufordDalt ( $14.50)
Seat 8: Clev520 ( $14.70)
Seat 9: jbr1000 ( $54.45)
Seat 10: BaileysDead ( $69.32)
Pistachio79 posts small blind (0.10)
BufordDalt posts big blind (0.25)
** Dealing down cards **
Dealt to s1Lv1a [ 5d, 5s ]
Clev520 folds.
jbr1000 folds.
BaileysDead calls (0.25)
RenatoGomes folds.
JustMutt calls (0.25)
ace_white folds.
s1Lv1a calls (0.25)
KINE_STUFFS folds.
Pistachio79 calls (0.15)
BufordDalt checks.
** Dealing Flop ** : [ 5c, 9s, 6d ]
Pistachio79 checks.
BufordDalt checks.
BaileysDead checks.
JustMutt checks.
s1Lv1a checks.
** Dealing Turn ** : [ Js ]
Pistachio79 checks.
BufordDalt checks.
BaileysDead bets (1.20)
JustMutt calls (1.20)
s1Lv1a raises (3.50) to 3.50
Pistachio79 folds.
BufordDalt folds.
BaileysDead raises (4.60) to 5.80
JustMutt folds.
s1Lv1a calls (2.30)
** Dealing River ** : [ 4d ]
BaileysDead bets (5)
s1Lv1a raises (13) to 13
BaileysDead calls (8)
** Summary **
Main Pot: $38.05 | Rake: $2
Board: [ 5c 9s 6d Js 4d ]
RenatoGomes balance $26.70, didn't bet (folded)
JustMutt balance $21.26, lost $1.45 (folded)
ace_white balance $21.65, didn't bet (folded)
s1Lv1a balance $43.80, bet $19.05, collected $38.05, net +$19 [ 5d 5s ] [ three of a kind, fives -- Js,9s,5d,5s,5c ]
KINE_STUFFS balance $28.75, didn't bet (folded)
Pistachio79 balance $79.80, lost $0.25 (folded)
BufordDalt balance $14.25, lost $0.25 (folded)
Clev520 balance $14.70, didn't bet (folded)
jbr1000 balance $54.45, didn't bet (folded)
BaileysDead balance $50.27, lost $19.05 [ Jc 6s ] [ two pairs, jacks and sixes -- Jc,Js,9s,6s,6d ]

If you aren't going to bet that flop, when are you going to bet?

DEFINITELY bet that flop. I can understand checking OOP in hopes of a CR but you are last to act here. You have to bet. Even though there are no flush draws there is a straight draw and a few gutshot draws. With 4 other people in the pot you don't want to slowplay anything short of a boat IMO.

As for the rest of the hand, you have to raise more on the turn. I don't like to think of it as value betting at this point so much as protecting your hand. That Js brought a flush draw and a new straight draw out. You have to give these guys bad odds here. Raise to $5-6, and try to get it all in on a harmless looking river card. As you played it though, I think the river raise is fine. I might have made it $15 but $13 is good too.

I raise pre-flop to build a pot, steal the button, take initiative for steal equity and a free turn card if I want.
I bet the flop because I'm aggressive and weak players checking to my button is a license to bet.
I don't stop raising the turn until he cries uncle or we're all-in.
I push the river and expect to be called
I raise showdown too

To reiterate what everyone else says - bet the flop. The main thing is nobody at 25NL sees the hit set so long as you don't just push AI right on the flop. Especially with that many people in the hand and a straight draw (at least) available, you want to value bet there. Personally I like to slam down a bet to see who's willing to play ball - so a value bet - and ramp my bets up afterwards accordingly. You probably coulda pushed on the river and been called since almost all fish cannot lay down 2 pair for their life. A very large amount of my set winnings come from guys who hit 2 random pair and can't lay it down when I go AI. Also, the op's $5 river bet to me at least says he's willing to go AI for this pot. (I know this is easy to say in retrospect though!)

I wanted to bet the flop, but according to my knowledge the table has played really tight and I didn't want to lose him too early. Considering the fact that I didn't bet the flop only because I had a strong feeling my opp would fold, Luckily he caught two pair on the turn and I was able to get some action. I agree with you on the turn bet that I made could've been a little more. And your right the flopped set was in disguise so I should've value bet regardless if my opp will fold or call.

Originally Posted by Off5th

I wanted to bet the flop, but according to my knowledge the table has played really tight and I didn't want to lose him too early.

Originally Posted by Off5th

BaileysDead balance $50.27, lost $19.05 [ Jc 6s ] [ two pairs, jacks and sixes -- Jc,Js,9s,6s,6d ]

Nice read. If you mean post-flop tight, then tight/passive play is giving up way too much. I'm raising Mr. J6o with a wide range, pushing the set farmers out of the hand, making him fold when his dogshit hands miss and out-playing him when we both hit.

Originally Posted by Fnord

...
I raise showdown too