Critical appraisal please

[TightEnd]

He had 

[Sheriff Fatman]

I sort of expected him to be on a flush draw, but only from the way you phrased your posts, not from the way the hand developed.

I think your query regarding looking to make a 'value bet' gave this away.  As I said earlier in the thread, a lead on the river is more of a defensive blocking bet than a value bet.  I think, at the time you're in the hand, you probably think the same thing.  Then when he reveals a missed draw you suddenly think you missed a value bet after all.

Sheriff

[totalise]

what is the thought process I should be adopting in deciding whether this is a value betting spot or not?

look at the action preflop, and put him on a range of hands that can call preflop. Make sure you do this honestly, rather then doing it to justify a river bet. base this on experience with him, or of experience with reasonably competent players. Obviously the stronger the read, the more accurate your assesment will be, and thus your actions in the hand will be clearer. Then ask yourself of these hands, how many of them will call a river bet with a hand that I can beat. if the answer is not many, but they figure to have a pretty wide range, then letting them try and steal it on the river/inducing a move by the fabled weak lead is preferable. Its not just a case of how much you are willing to commit to the hand, but a case of how, and calling in these spots gets you a better return on your money then being the bettor, for obvious reasons.

[The Baron]

Just to play devil's advocate...

I quite like the check call on the turn from you Rich. If he had something like AT it would have scared him half to death and most likely caused a check behind you on the river rather than a scary all-in. After that call from you he will surely only bet the river now other than with a hand that beats you? I'm not saying I would have check called here but it worked quite well.

The check raise on the turn is the obvious move I think, but you're only committing more of your stack to a loser or scaring him off if you are the winner.

The river is also a check call from me I think.