[Hobbs.]

James,

Nice post.

There's kind of lot of stuff I want to respond to, but my thoughts are kind of jumbled right now so I don't quite now how to start getting things out in a coherent manor.

I'd say the big thing is I'm not convinced even if he need to bet/call the turn here that betting isn't the best play. Writing out the math isn't really helpful because we will end up just assigning arbitrary weights to each scenario. A quick back of the envelope calculation though that seems conceivable is as follows:

assume there is a balance between the money made from hands he calls the turn and folds the river with and times he bluffs the river when you check behind the turn. This seems like a decent assumption to me as he's likely to going to call a bet on the turn with fairly little equity and I doubt he's bluffing with every hopeless hands that he sees the river with.

Now we are left with the balance between the 2 bets we collect when we value bet both streets with the best hand, the 2 bets we lose when we bet turn/river with the worst of it, and the 3 bets we either when or lose when he raises the tunr and we call down. Of course this is way too simple but these seem to be the major considerations. So looking the above it just seems that if we are forced to call down a turn raise from this guy it's because he is bluffing too often and considering this guy is kind of a monkey turn EV from betting twice and getting called twice should be pretty close to 2bb (maybe 1.5) that betting seems like the better option.

I hope I was at least clear enough in that ramble that some decent thoughts can be extracted from that.