1; It's a bad beat.
2; yes you played it bad. The button has re-raised you 2x now..this means he is very likely to call a re-raise from you..so what's with the bet-calling? Re-raise him again..he is bound to call.
Looking back on it now, I agree more of a check to a raise and smooth call?
I don't quite get what you're saying above. I think leading out here is good (so would never check it against this oppo) but I'd re-raise him again as I think he'd call. I wouldn't check raise...I want him to get as much money as possible in the pot.