[lil']

OK, I'm very good at limit, but my tournament play leaves a lot to be desired, as I think this hand demonstrates.

I decided to try out a $50 2 table sit n' go at Party. Things are going well. There are 7 of us left and the top 4 get paid. I am in first by over 1500 with about 5500 chips. Blinds were $100 and $200

I am in the BB, and the CO-1 open raises to about 600 (he had about 3600 chips). The more astute players had been open raising to steal the blinds with anything decent, and I could be fairly certain he had some combination of face cards. I have 8-8 in the BB and it's folded to me.

I had no idea if I should push all in here or not. I had pushed all in several times before against this guy and forced him to fold earlier, and I had an aggressive image at the time. I figured this was very likely a coinflip here, and that I would be called due to my image. I decided to call and attack a flop with no ugly cards.

The flop comes 9-10-4 rainbow. It's probably safe. 1300 in the pot. I have about 4900 left, he has about 3000. I check, he overbets the pot with a 1500 bet, I push in and get called by K-Q. He rivers a gutshot and I lose.

2 questions...

1) Was my pre-flop thinking sound? Was pushing in a better move? I was fairly certain in my read that I was against two overcards, probably jacks or higher.
2) My flop play was really bad, right? By letting him bet a large chunk of his stack, I'm getting into a situation where I am going to be called. If I was going to push, I should have done it right away and not checked, right? Was continuing with this hand a mistake?