What is the bottom of your calling range there ? I rather 4b 2x, 2.2x a hand like this since he is 3betting too much and has some ok blocking value. 

I understand your raise OTF against the tiny bet but what you are representing a very narrowed range, basically 88s, 66s and A8 but none of this hands plays better raising than calling this flop, I think. A8 blocks the best part of his continuing range and Ax are huge equity dogs against the sets. With this stats he should barrel off AK/AQ and even AJ, since some of the top of these are in our 4betting range. 

I do realize that I represent nothing at all, but I figured he is not going to mess around all that often with all of his missed hands. They just simply bet and then they fold to action. FWIW, I do balance this by raising very occasionally AQ AJ.

I am pretty sure that having a raising range is better than none, but I would construct it on some T9s, 75s, 86s, 54s with bdfd. I think it plays better on later streets and against a click back or some standard raise size, since it does not block the major part of his offsuit combos that will continue. 

Haha this is terrible but I love how ballsy you played it! 
Raising flop doesn't make much sense here as a play unless you're flatting big Ax preflop which you aren't.  Sometimes when your range is behind you just need to play a little more straight up.  The standard way to play back at his 21% 3b range + high cb freq is to call with marginal hands that can win sometimes at showdown and sometimes by bluffing- good examples are KQ, KJ, various cards above an 8 with a bdfd and 77-TT.  To be honest though, he's actually playing quite well in this spot, and by overdoing your counteraggression you're hurting yourself too much to put him in tough spots.