[stigmata]

OK I'll have a stab at this even though I'm probably wrong

1) From the desribed player, lets assume he can only have KK/AK here (sounds like he would coldcall 99, and AA isn't that likely). Therefore there are 3 ways he can have a hand that beats you, and 6 ways he can have a hand that you beat. This means the EV of re-raising and calling a 3-bet is effectively neutral (2/3 * 1 == 1/3 * 2).

If your going to re-raise him at some point, I prefer the turn. This removes the possibility of him checking down the river. Also, if we can fold to a further raise this would be the place to do it. Obviously you can't fold (because of the river crying call). Therefore, with both re-raise/call being effectively EV neural, I prefer the lower variance path of just calling. Perhaps donk-betting a scare river (which didn't come) to stop a free showdown.

2) Wouldn't he take a free showdown with an underpair? What are you beating? KT?