[ZootMurph]

Two things make this hand so difficult for me: the history between you and villain and the coordinated board. He could literally have any two cards.

I think check/fold is the worst option. But also the smallish bet on the flop just smells like weakness, and I don't think is a much better option, especially if every other hand you've been in you've bet strongly. The sudden small bet from a TAG on a coordinated flop is a definite sign of weakness. I wouldn't believe a TAG was trying to trap on a coordinated board. If you had AJ or something like that, you'd be giving odds for straight and flush draws. So my read on you would be that you are hoping to take it down with a whiff or a weak draw.

If I were in Villain's position, I would read it as weak and make a raise, no matter what my holding. So, to me, the small bet is asking for a raise, and the raise can mean anything.

So, all that considered, I'd make a bet of no less than 800 on the flop. I think headsup, with a call from a guy you've been pushing around a bit doesn't mean much, and your second pair is good most of the time.