(1) Why in the world would we 3bet? Being ahead of his opening range has no bearing on whether we should 3bet or not. It only matters if he's continuing with a range we are ahead of, or folding better hands often enough. I believe a call preflop here is pretty standard.

(2) The flop raise isn't 'bad' per se; however, there are a few things. This flop does hit him pretty well. 44, 65, 77, 88+, 87, T9, etc. Sure it doesn't hit his broadways, but he can still have quite a few strong hands. I'd probably raise, or maybe float, not really certain which is most +EV.

(3) Turn is meh.. I can see merits to checking behind, as well as bet/folding turn for value/protection. I'd change it up depending on how likely I think he is to continue with worse like 99+, 76, etc. The bad thing is I expecthim to play most of his nut hands like this, and not sure if he calls much worse since the "scare card" hit.

(4) Yeah, just call river. As I said, he likely bet/calls, checks turn with the majority of his range, which contains 44, 77, 88, 87, so you could very well be ahead of him on the river, but if he doesn't call a river raise with worse (99-KK, 76, etc), then a raise is no good. And I think that's prob the case.