Ok, so preflop, I would advise never to openlimp anything barring extreme circumstances.
Generally you want to openraise small with a wide range, because people usually overfold (free money), and only 3bet with a very tight range. This means you have to open small with your whole range, even "scary" ones like JJ
. Obv, when you have a very aggro player behind you, you need to tighten up substantially.
Obviously there are not many hard and fast rules in poker, but if you are going to openlimp with KK here, it needs to fit in with a an overarching strategy of openlimping with lots of hands, and I struggle to see how this strategy would be profitable.
Once he raises pre, just jam. If he has a strong ace, or medium pair, he will more likely put more money in bad preflop than on the flop. Again, what other hands are you going to play like this in a profitable way?
Flop. Just get it in. You are overcomplicating this hand.