[JrJordan]

AKs is still a fold most times vs. these players/positions, but a few subtle changes could tip the scales.

Ragged flops aren't all equal in this case. In partiuclar, is it a 7xx board where my CRAI on a flop can get called by 88-TT or Txx where I'm only getting called by better hands?

Heads Up with Button:
On a 7xx flop: I CRAI without too much hesitation and expect to be called by 88/99 given he's getting over 3:1 at this point.

On a Txx flop: A bit tougher since I almost feel pot committed if I put any money in on the flop, but I'd really consider calling flop and check/folding to a turn push. This would be a more default play if the flop bet was closer to 100-120 (which seems to be the default flop bet in a 3bet situation more often than 140-150). Given the $150 bet it's a tossup between the c/c line described or CRAI.

Multiway: I wimp out when I get the chance. If it gets checked to Button on a ragged board and he still bets 140-150 I'm likely folding. Good TAG has to expect any overpair at that point to call at least one street multiway, so he's not bluffing overs or value betting smaller overpairs often enough for calling to be good.