This thread has a thousand replies already and no doubt the 'correct' play has already been determined. But before reading these I thought I'd give it a shot (reading replies I normally agree with 1 or more of them and then find no need to say anything - hmmm, is the term grunching appropriate here?)

My first thought is don't be so down on yrself! If your feeling bad about the way your playing then tighten up, be less agressive. That'll save some bets and won't exagerate any downswing you might be having. After a few wins you'll think damn, I shoulda raised there and you'll feel a warm glowing warming glow about your play when you do.

On the hand specifically, you give a good reason based on a read to raise PF so fair enough (I wouldn't do it but I'm pretty weak).

I think a check on the flop is better. Villian could check-call holding a queen, jack or even a weak ace. Chances are he has one of them. You get little information from the bet and really are just hoping for a fold. If you have the best hand at the flop you'll probably have the best hand at the river, so I'd check.

Turn, again I'd check and snap off a bluff at the river - or else check it there again.