[Ikke]

I would have check-raised the flop here. Basically, I think if you get aggressive on the flop here you're most likely to get the best reward/risk ratio if you consider his whole hand range and is the least exploitable (did that make sense? having a hard time putting it in words).

With this kind of flop he really needs to be suspicious and therefore can't let go of many hands. The same applies to you...you should get to showdown on this hand. Check-raising the turn will likely make HIS play easier...he's likely to 3-bet with better hands than yours and you can't lay down. He might also make a decent laydown with A high no diamond or check the turn through with a better diamond no pair.

You give almost no info away by check-raising the flop. Yes, he might make fancy turn plays but you shouldnt mind that. They won't add much to his EV because your hand is quite uncertain for him and you're not going to lay down. For instance, he could easily make the raise the turn check the river play. You don't mind that...your likely optimum EV against his handrange is when 2 big bets go in after the flop anyway. Hope that made any sense as well.

Where it comes down to is that by check-raising the flop I really feel that you extract most against lesser hands and lose less against better hands. It's IMO approaching the optimal play. This might change if you have a strong read on the player though. For instance if he really is in the mode of pushing you around. Then you might want to give him the best opportunity to do so. But to decide that I should have been there.

Regards

BTW...I would also strongly consider 4-betting preflop.