Re: 50/100 Deep
I think that you should go a head and stick it in preflop. Yes you will obvisoulsy be giving the strength of your hand away there is enough money in the pot to compensate for any lost action plus how likely is he to get away from KK PF if you push. Not likely unless your the tightest stiff at the table and only RR AA. Which based on your observation doesnt seem to be the case.
While the flop does suck. Think you have to take the play away from him by betting if he pushes your essentially pot commited anyway and if he does have a set your at least drawing live albeit slim but live non the less.
If you check and villian bets cant just call since depending on the size of his raise will most likely pot commit you. CRAI and hope to suck out.
Sounds a little amateurish but not to many options given the size of the pot and both chip stacks as well as the size of his future bet on the flop.
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