So according to Poker stove your a 51% to 48% favorite preflop and 44% to 54% dog on the flop. Its easy to second guess after the hand, more important during, and like tommyhawk said the preflop raise of $1K to win $300 on the bubble with the short stack might be a bit much. Hard to say without knowing what the average preflop raise was at that point.
I'm suprised he called a preflop raise of $900 with those cards and his stack and then all-in with a flush draw. I've seen it happen many time though, sometimes it feels like they always hit their flush or in this case the higher pair, and then get it rubbed in your face when he hits a second pair on the river, as if to say ha ha on you. Sucks man.
I tend to be more conservative in a spot like that, if he was loose aggressive (appears so) and you wanted to play the 99 hoping for a set then a 2x or 3x, BB raise preflop would work, perhaprs his aggressive would cause him to push harder and you could make a decision from there. You made it an incorrect call for him to chase by going all in, he was getting whatt? Like 2-1 and needed at least what 4-1 to call, right?
I'd say slow it down, based on that one play I'd say he's a donk, let them bust themselves out until you get the money spot, then push those medium pairs.
Curious - Anyone think he should have limped in?
ComicFx