Villian is 27/8/2.60 in my DB over 100 hands but he's on 4 of my 8 tables so I assume he's a regular.

PokerStars Game #7182117895: Hold'em No Limit ($1/$2) - 2006/11/26 - 10:14:42 (ET)
Table 'Menkib II' 6-max Seat #4 is the button
Seat 1: clarky12 ($423.35 in chips)
Seat 2: GodlikeRoy ($199 in chips)
Seat 3: happyclammy ($247.90 in chips)
Seat 4: vwxyz ($314.40 in chips)
Seat 5: jespered ($115 in chips)
Seat 6: garbage1340 ($129 in chips)
jespered: posts small blind $1
garbage1340: posts big blind $2
*** HOLE CARDS ***
Dealt to GodlikeRoy
clarky12: folds
GodlikeRoy: raises $6 to $8
happyclammy: calls $8
vwxyz: folds
jespered: folds
garbage1340: calls $6
*** FLOP ***
garbage1340: checks
GodlikeRoy: bets $20
happyclammy: calls $20
garbage1340: folds
*** TURN ***
GodlikeRoy: bets $48

Ive tried this a million times when theres a flush draw on the flop and it almost never works. It seems I always get raised.

For the same reason that you want to fire again here, Ive started just calling the flop on boards when theres a flush draw but I know I have the best hand. They always want to fire again thinking youre drawing.

I am not sure if I would fire on that flop against 2 OP, (though it depends on your image) one of them is going to call me almost always, even with A-high sometimes.
As to a second barrel it is very read dependent, without a good read I'd rather not to because of bad position.

check is your best bet here and evaluate after that

Yes, fire again around pot...FDs will fold (based on your limited read) and if he floated, he'll be more inclined to believe you and fold. This hand also sets up future hands so he won't float you light.

Just read the other responses and the result...seriously, I see so many light floats here unless they're donks who can't fold 22...but even good players who float with the underpair will fold if you show more strength on the turn...showing strength on the turn after a called CB on the flop is a very powerful move both in the hands themselves, as well as for metagame issues.