[Eeegah]

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That's the problem with checking here IMO, not that he might check behind but then he might raise a bet.

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Let's contrast with a hand I had last night.

I have a weak flush draw in the BB, 8[img]/images/graemlins/diamond.gif[/img] 3[img]/images/graemlins/diamond.gif[/img] on a 3 handed 9[img]/images/graemlins/diamond.gif[/img] 2[img]/images/graemlins/diamond.gif[/img] A[img]/images/graemlins/heart.gif[/img] 3-handed flop. I couldn't bet for value since there was just the two of us, but the only guy who limped (SB completed) bet both the flop and a blank on the turn.

River gave me my fifth diamond. I think this would have been the perfect opportunity to checkraise, as donkbetting the third diamond would have made it perfectly clear why I was calling down, and I could easily trap the SB if he's coming along.

Unfortunately I whiffed, but I don't think I would have won any extra had I bet out.

In your hand, you've been showing aggression on every street. You're apparently assuming that you can get a made flush to bet out or induce a bluff, but (a) it's pretty obvious you're not folding here and (b) the pair on board could make someone weary. If you'd been playing this strongly and suddenly stop at the third heart, he might suspect that you had a boat and were looking to trap (this would likely be MUBS but it's a possibility, especially if it were a weak flush). There's also the most likely scenario--he doesn't have a flush. He could have a busted straight draw, in which case he won't be helping you trap, or A-rag, which if he's dumb enough to call to the river with he'll likely be passive enough to be scared of the flush.

In summary, check-raising the river works best if you haven't been showing aggression previously and can trap the field, as your opponent wouldn't expect your bet but might fold outright if you donk. When you're going RAAAAAR to the river and wimp out, people start smelling rodents.

(FWIW villain in my hand had limped AKo and deservedly lost.)