Turning Stone hands - ew @ losing live

I got my ass kicked. But - I don't know if I played too badly for my first time live, maybe I just run bad... overall, I was missing a lot of hands I raised, and missing a lot of flops in limped pots, getting re-raised w/ TPNK... etc... But that's not really important.....

Only two hands really interest me:

My opponent is, at least, 'acting' like an arrogant douche. He is playing a lot of pots, checking every hand in the dark, looking away from the flop and checking, talking about how he plays 20 tables online, raising like 10x BB, calling tons of raises, etc. He's on my left.

I raise 77 5x BB, he calls, everyone else folds. This is pretty soon after he busted my aces all in preflop w/ A9s - so I figure that might enter into his decision making, but I am not sure.

Flop comes 833 , two of same suit. It ends up with him betting a good amount on the flop, and I insta push for $100.00. Now my thinking was: he might think I am tilting and have a bad read on me, His range would seem huge based on amount of hands he is playing, I think he might call with FD / overs, or just fold. I don't think he has a pocket pair >77.

A little bit later:

I raise 99 vs him, and he calls. Flop comes xT7, I bet - he calls. turn 4 - putting a FD on board. He bets, I just call. River comes another 7, misses the FD, but he insta pushes.

Am I overthinking if I'm considering calling here?

First of all, I've been to the following B&M's:
Turning Stone
Seneca
Niagara
Fallsview
Rama

All in the Ontario area... Turning Stone is by far my favorite.

In regards to the 77 hand: I think this is a standard play.

In regards to the 99 hand: Stack sizes would be great info in making decisions. Also, the call by you would depend on wether or not you think he has a better hand than you OBVIOUSLY. Unfortunately, I can't tell you better than you can tell yourself, what the best option is. You know more about the table dynamics, reads on villain, your table image, how much villain has had to drink, etc. Generally, a good rule of thumb is to camp vs maniacs.