playing OOP sucks. Playing this OOP sucks even more.
I'd be tempted to fold here just to avoid getting in a large pot with a marginal hand OOP, but given the action, and the mistaken check on the flop ( i bet that flop 95% of the time), i have no idea.
The biggest issue in my mind is a draw. If he's got one, he's probably not going to fold to a check raise. That means that if you raise, I expect you to be called by every hand that beats you, and by draws. maybe some combination of the two like
[8s]. Or possible
[9s]In other words, I don't think a CR wins you the pot very often unless the guy is bluffing.
So in this case, i'd have to decide between calling his bet and re-evaluation based on what card the turn brings and on what he does after that, and just folding here.
I think, being OOP, the best decision is just to muck, and take more care with these hands to bet instead of waiting to call a bet OOP.