Re: 50/100 double gutter
What's up with his small preflop 3bet? I know you've said you've never seen him make it, but it seems kind of strange and I'm not sure if he's doing it to entice a big fourbet from you or with some hand that just thinks you're stealing. Also, while I love double gutters as they're often well concealed, this one isn't, since if you turn a 6, I can't see him paying off that much.
Given stack sizes, I still like a check to see if he'll lead weak or strong. You could call a pot sized flop bet and possibly a decent sized turn bet as well if you think he's paying you off, but I think the only cards you'll want are a ten unless you plan on bluffing a set, in which case a turn checkraise or something could be kind of sweet.
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