Analyze a hand through my eyes: Question 1

[Unrelated poker thought: I use Poker Academy to practice cash game play when I'm not on a net connection.  It's AWESOME, but I'm good enough at reading my table now to tell that it doesn't model the mood of the table at all.  When 9 or 10 people first sit down to play, they're on their best game, and the weakest ones deteriorate as the session grinds on, playing poor hands and calling raises they shouldn't because they've lost money and are tilting, or because they've sat too long and gotten bored.]

In this description I’m going to refer to the players defined by their seats in relation to the button.  Assume the dealer button is in Seat 10, and the blinds are Seat 1 and 2.

I’m first to act (Player 3) at a 10 handed $1/$2 no limit table and am dealt a pair of red queens.  I have about $330 or so in my stack, and I have every player at the table covered for chips.  The table thinks I’m tight.  The table is moderately talented, and generally if two people call a moderate raise, a couple more call it "just for odds", even if they know they are behind.  (Note that I think this is a high variance mistake for my style of play.)

I raise it immediately to $7.  For this table that’s a notable raise.  $11 is the high end.  Seats 4 and 5 fold.  Seat 6 makes it $15 to go with about $275 left.  He’s slightly unhappy with the fact that he’s only about $30 up for the night.  He’s sober and has been stealing small pots with $10 bets on raggedy flops all night.  Something about this raise seems unusual.  He’s likely to get callers, but with what is he holding that makes a min raise correct?

Seat 8 cold calls the raise.  Seat 8 is a talented and very drunk player.  His tight aggressive game while drunk is better than mine sober. I’ve been watching him steal small pots all night, as well as smelling traps and folding.  He has about $270 after calling the raise.  I think this is a loose call on his part, as his MO is about stealing the pot when the flop misses everyone.  To his credit, he has position on the raiser (me).

Seat 9 folds, and Seat 10 (the button) looks down at his cards at a pair of red fours.  His stack is about $250.  He is a generally tight player who is terrifying in that he’ll pay big to draw, which means it’s dangerous to give him free cards.  I do not think this is a good habit.  He also plays his good hands strongly, forcing you to pay heavily to draw against him, which is a good habit.  He’s not drinking.  Everything about him suggests he’s a talented player, very comfortable thinking through his decisions before acting.  He’s not a young aggro, but about 35 or 40, accomplished, and completely in control of his game.

Question #1 : The pot stands at $40.  What should he do with his 44?