I think a bet is okay here. Not sure if it's amazing but because this board is so disconnected, he can call with a 6 or a 3, 55, 44, AT, KQ, KJ type hands will usually peel, etc. ...

When he check/raises me I wonder if we're in a shove/fold spot. I can't imagine he's going to bet smaller than a shove on turn if I call, but there are just a ton of hands he can do this with that are weaker than 77. I elect to call, planning to call most turn shoves.

And here we are. Was the flop call a mistake? Was it fine and we just carry out our plan and call the shove? I mean if he raises flop with KJ, 87 or something, I can't imagine him not shoving here. But if I shove flop then I take away his ability to bluff here, so I don't think I want to do that.