Badly played set followed by badly played draw?

[Inevitable]

First orbit, no reads on Villian. I feel like I should have called, checked and made a river bet if he checked behind me otherwise check/call, check/raise on the river. I felt like, my raise would have been the accepted line. What made me feel like the raise line wasn't the most EV one was that he thought for a long time and said "hmm..." and then "nice hand" as he folded.

PokerStars No-Limit Hold'em, $0.25 BB (5 handed) converter

UTG ($10.75)
MP ($7.70)
Button ($16.75)
Hero ($26.05)
BB ($25.45)

Preflop: Hero is SB with 8[img]/images/graemlins/diamond.gif[/img], 8[img]/images/graemlins/club.gif[/img].
<font color="#CC3333">UTG raises to $0.75</font>, <font color="#666666">1 fold</font>, Button calls $0.75, Hero calls $0.65, <font color="#CC3333">BB raises to $1.25</font>, UTG calls $0.50, Button calls $0.50, Hero calls $0.50.

Flop: ($5) 7[img]/images/graemlins/heart.gif[/img], 2[img]/images/graemlins/spade.gif[/img], 8[img]/images/graemlins/spade.gif[/img] <font color="#0000FF">(4 players)</font>
Hero checks, BB checks, <font color="#CC3333">UTG bets $2</font>, Button folds, <font color="#CC3333">Hero raises to $8</font>, BB folds, UTG folds.

Final Pot: $15

One hand later... Same villian.

PokerStars No-Limit Hold'em, $0.25 BB (5 handed) converter

BB ($7.50)
UTG ($7.70)
MP ($15.50)
Hero ($31.40)
SB ($24.20)

Preflop: Hero is Button with Q[img]/images/graemlins/club.gif[/img], K[img]/images/graemlins/diamond.gif[/img].
UTG calls $0.25, MP calls $0.25, <font color="#CC3333">Hero raises to $1.5</font>, <font color="#666666">1 fold</font>, BB calls $1.25, UTG calls $1.25, MP folds.

Flop: ($4.85) 9[img]/images/graemlins/diamond.gif[/img], J[img]/images/graemlins/diamond.gif[/img], 8[img]/images/graemlins/diamond.gif[/img] <font color="#0000FF">(3 players)</font>
<font color="#CC3333">BB bets $2</font>, UTG folds, <font color="#CC3333">Hero raises to $29.9</font>, BB calls $4 (All-In).

Turn: ($40.75) 5[img]/images/graemlins/club.gif[/img] <font color="#0000FF">(2 players, 1 all-in)</font>

River: ($40.75) 3[img]/images/graemlins/club.gif[/img] <font color="#0000FF">(2 players, 1 all-in)</font>

Final Pot: $40.75

I thought a gutshot and flush draw was strong enough to push, was I wrong here?

[OatmealJoe]

The first hand I'd check raise the flop, but maybe slightly less (to $6 or $7).

On the second hand I don't see any problem putting him all in on the flop, especially since he has such a small stack. For all you know, your K/Q might be outs as well.