Well, I'd say it's a flip. But I would also think that maybe there is a chance he is just sick of your three bets and be spazzing out. I think it seems  like his range is a bit wider because of that. I gave him 77+, ak, aq, a10s and kqs (Which I still think is a bit tight, considering the history) in Poker Stove.

Text results appended to pokerstove.txt

   1,664,359,488  games     0.031 secs    53,689,015,741  games/sec

Board: 

Dead:  

equity win tie       pots won pots tied

Hand 0: 53.288%  47.07% 06.22%      783399504 103503318.00   { AKo }

Hand 1: 46.712%  40.49% 06.22%      673953348 103503318.00   { 77+, ATs+, KQs, AJo+ }

Looks like the numbers give you a decent edge. If you win, you'll have a really nice stack. If you lose … 

I think either is fine, though you really have him set up to spazz out. If you have a long term plan going on this guy, which I think you do, how can you not pull the trigger? I think I'd hold my breath and shove and fist pump when he turns over AQ and bricks three streets. Were you feeling lucky?

When you 3bet there what was your plan against a standard 4bet? If you were planning to fold then I don’t like the 3bet, if you were gonna 5bet jam then I’m fine with it.

In terms of ranging him, yeah he may be getting pissed off and decide to jam but from the sizing I think this is gonna be 99-QQ and AQ+ (maybe wider like 77-QQ and AJ+, prob not tighter), ie hands he is scared to see a flop with, I doubt this is KK+ very often at all and tbh I think it’s weighted towards AQ+. From what I can tell you are having to call 26k to win 35k. I would make the call.

One extra thing is I would make the 3bet sizing bigger there, you are against an open and a flat, also you are OOP, I would make it more like 4.4k in general, or even slightly bigger to make it look like an obvious squeeze (to then call off). IMO your sizing is just going to encourage both players to flat a lot of the time and then you are playing a bloated pot OOP.