[KurtSF]

For the sake of argument, let's take his 3-bet range as 99+, AK, AQ. You crush 99, TT, are crushed by AA, KK, QQ, are slightly ahead of AK and AQ (and a toss up against JJ, A[img]/images/graemlins/heart.gif[/img]K[img]/images/graemlins/heart.gif[/img], A[img]/images/graemlins/heart.gif[/img]Q[img]/images/graemlins/heart.gif[/img]).

With this range I think shoving is a suuuuuper high-variance play, and probably in the end -EV (since you get called more when you're crushed). That said I do think you're ever so slight ahead (anyone want to stove it?) and should push your edge. Frankly, GM is very aggressive and will force you to make these high variance plays to get the jump on him. If you're not rolled for high variance play against GM you should avoid big pots with him and fold the flop I suppose.

Now moving on, the thing is, is that I suspect his 3-betting range is bigger than what I assumed above. You are ahead of pretty much the entirety of the "expanded" range, as there's few monsters on this flop that make it in. For instance, I doubt 33, 44, 55, or A2 are ever in GM's hand here (though 67s might be). So if his range is wider (suited connectors, 2 big cards, etc.) what is added (in addition to 99+ AQ+) is air and flush draws.

BTW, good OP. Looking forward to reading more.