Could I have extracted more? AKs in BB, NL $500-max buy-in

[SpeakEasy]

NLHE, $100 min, $500 max buy-in, full 10-handed table. I just sat down about 4 hands earlier, and I have the full $500. Blinds are $2-$5. Button has $2000+. Others involved in this hand have average stacks in the $400-$800 range. Played with a couple at the table before, but not with anyone involved in this hand, so no read on any players yet.

I am in the BB with A[img]/images/graemlins/diamond.gif[/img]K[img]/images/graemlins/diamond.gif[/img]. UTG raises to $20. Five others(!!) call, including Button. SB folds. I check.

Flop: A[img]/images/graemlins/heart.gif[/img] 8[img]/images/graemlins/club.gif[/img] K[img]/images/graemlins/spade.gif[/img]

I check. Everyone checks to Button. Button bets $50. I raise to $150. Everyone folds to Button. Button thinks for a good while, then folds, saying “Nice raise.” I win $190 pot.

I can’t get away from the thought that I could have won more on this hand. My questions:

1. Should I have re-raised pre-flop? A re-raise would certainly have been called by several unless it was big, but a re-raise didn’t seem warranted with this hand in BB after all those callers.

2. Should I have bet on the flop and re-raised if button raised? If I had open bet, it would have been half the pot or more to push the drawing hands out. I was only concerned about KK or AA at this point, which would probably re-raise my opening raise and let me know where I stand(?).

3. Should I have just called Button’s $50 bet or raised the minimum to bring him along and extract more?