Extracting value

*sigh*. I think I misplayed this one... since I lead out on the flop, should i have lead out on the turn as well? It's hard to get any real value out of checkraising a minbet. If I raise too much he quits. If I flat call I pretty much have to lead out on the river.

Opp was loose and limped into pretty much every single pot PF. He also tended to call many flop bets (incl. potsize) if he caught any piece of the flop or even held overcards! I had real difficulty putting him on a hand - he'd play just about any 2...

#Game No : 2817064985
***** Hand History for Game 2817064985 *****
$25 NL Texas Hold'em - Monday, October 03, 04:12:45 EDT 2005
Table Table 37559 (Real Money)
Seat 10 is the button
Total number of players : 10
Seat 5: tank_MB ( $41.49 )
Seat 9: crschau ( $61.51 )
Seat 2: ME ( $36.15 )
Seat 6: raol79912 ( $43.80 )
Seat 7: obilawn ( $25 )
Seat 10: arayante ( $10.70 )
Seat 8: pokeristen ( $23.30 )
Seat 3: cmoney322 ( $27.15 )
Seat 1: cnahum7 ( $39.85 )
Seat 4: larssmoker ( $25 )
cnahum7 posts small blind [$0.10].
ME posts big blind [$0.25].
** Dealing down cards **
Dealt to ME [ Jh Th ]
cmoney322 calls [$0.25].
larssmoker folds.
tank_MB folds.
raol79912 raises [$0.50].
obilawn folds.
pokeristen folds.
crschau folds.
arayante folds.
cnahum7 folds.
ME calls [$0.25].
cmoney322 calls [$0.25].
** Dealing Flop ** [ 5d, Td, 5h ]
ME bets [$1].
cmoney322 folds.
raol79912 calls [$1].
** Dealing Turn ** [ Ts ]
ME checks.
raol79912 bets [$0.25].
ME raises [$1].
raol79912 calls [$0.75].
** Dealing River ** [ 4c ]
ME bets [$3].
raol79912 folds.
ME does not show cards.
ME wins $8.35

I don't see what's wrong with this.

You just can't expect him to put much money in this pot unless he has the same hand as you (or better). You pretty much have the board crippled.

Given that, however, your river bet seems a little ambitious (over half the pot). Who's calling that without a ten? Maybe a six.

Personally i'd only bet $1-$1.50 on the river.