This never works. Why does this never work?

[manupod]

Villain is 24/15/3 over 300 hands, has raised enough of my cbets for me to think he's doing it with a ride range. But keep in mind that the flop is 4 ways so I'm not sure leading is best. He might be taking a stab at it, so I'm expecting the turn to be checked back a lot, or he'll bet and I'll have to call- but I rarely expect to be shoved on when I lead and it gives me fold equity, etc.

Thoughts on this and a better way perhaps?

Absolute Poker No-Limit Hold'em, $2 BB (6 handed) Hand History Converter Tool from FlopTurnRiver.com (Format: 2+2 Forums)

BB ($253.43)
UTG ($74)
MP ($425.65)
Offtheheezymanupeezy ($205.05)
Button ($197)
SB ($79)

Preflop: Offtheheezymanupeezy is CO with T[img]/images/graemlins/diamond.gif[/img], K[img]/images/graemlins/diamond.gif[/img].
<font color="#666666">2 folds</font>, <font color="#CC3333">Offtheheezymanupeezy raises to $8</font>, Button calls $8, SB calls $7, BB calls $6.

Flop: ($32) Q[img]/images/graemlins/club.gif[/img], 7[img]/images/graemlins/diamond.gif[/img], 2[img]/images/graemlins/diamond.gif[/img] <font color="#0000FF">(4 players)</font>
SB checks, BB checks, Offtheheezymanupeezy checks, <font color="#CC3333">Button bets $16</font>, SB folds, BB folds, Offtheheezymanupeezy calls $16.

Turn: ($64) J[img]/images/graemlins/heart.gif[/img] <font color="#0000FF">(2 players)</font>
<font color="#CC3333">Offtheheezymanupeezy bets $39</font>, Button calls $39.

River: ($142) 6[img]/images/graemlins/club.gif[/img] <font color="#0000FF">(2 players)</font>
Offtheheezymanupeezy checks or shoves??