If villain is extremely passive then he's going to be a weak player on average, meaning he can still possibly overvalue JJ-99. So I would begrudgingly call, but I'm not thrilled. He's going to have all the sets and ragged two pairs in his range too, so jamming is a clear overplay against such an opponent.

If we call and he shoves the turn I would find a fold.

How good is your read on this player? Do you have a good sample size on them? I mean if they are 16/4 over 2k hands then I'd be happy to fold the flop here, but if it's more of a general read of them playing passive for the session I go by Turlock's advice above and get it in.

Only thing I would add is I think I would be squeezing slightly larger. If they are passive like you say and going to call the squeeze with a wide variety of hands that you beat, why not get some extra value pre flop. I think I would have squeezed to like .70 here, maybe even .75. It would not have changed anything in this exact scenario and in fact you would probably be at a SPR of less than 2 so you are going to be stacking off regardless and if they have it sobeit.

I agree with Turlock in that you will find guys like this will overplay the mid overpairs to that board and will raise 99-JJ, maybe even a top pair hand like A8s or K8s that they called with pre cuz they were getting such a good price when the OR called your squeeze. I have seen plenty of guys GII on borards like this with TPGK, with 8,9,T, J high boards with an A or K kicker

On the flip side it is always incredibly strange to be getting raised on a board like this and as you say, a lot of times, from a player like this, it is a set. I still think you have to stack off. Even in this scenario your SPR is less than 2. After his raise he only has .39 behind. I guess you could make a really exploitable fold and save yourself 50ish BB, but I still think they can have enough combos of hands that you beat that GII is not a mistake.

Stack sizes here indicate we must go broke. You've to call another ~$1.65 (including your last raise for the final few cents) and the pot is already large, the price we are getting here would indicate to me that we should be going with our hand everytime. Villain was not getting the correct price (or anywhere close to it) to set mine so we are going to be killing him in the long run if they are making these kinds of preflop calls.If we were deeper then I would be more inclined to argue for a fold here.