Ummm.. This hand history shows exactly why I'm saying check/raising on a board like this can be a bad idea against thinking opposition. When he check/raises, he is really repping a very small range, one that he is likely to not even check/raise very often. Like he doesn't have any 2x combos in his range, and very few Jx combos. He obviously isn't going to stack off with his weakest of underpairs (55-88ish?), and he is going to be very timid about calling it off with 99,TT.

However, on the other hand if he thinks about it would you b/3b shove a Jx hand there? Or would you call and let him put it in himself on the turn? Likely the latter. As you would probably do with AA, KK, QQ if you intended to stack off (which I would facing a c/r here most likely). So by 3bet shoving here, I'm having a hard time putting you on any kind of a credible range. I could see villain getting brave here and calling with 99,TT, maybe worse.

And as far as playing aggressively on dry flops OOP. I don't really do it all that often. And you say you are talking about an individual that cbets often here. Well, it's imo that alot of individuals won't cbet the Q22r board all that often. I would think a majority of individual (given they don't have a tendency to cbet too much anyways) would check back alot of their SD hands, either conceding that you are likely ahead and they would have to fire multiple barrels, or they are likely ahead and can win at showdown but can't stand much aggression (and you likely don't call with worse).