You are bottom range and don't block some 98 Axhh combos but i think there is a problem with the bet size. He can't not have it enough of the times for you to risk such a large amount as a bluff. So idk, maybe have 1/3 bet otr and bet it very thinly with AA KK naked Q and a large bet with Jx as a bluff and all fh combos. That being said, they will obv never fold Qx even to a large bet, so bluffing river pot is bad. And since bluffing pot is bad and i think it's a very small chance they fold a jack to a third bet, probably never bluffing is best :P

What about just folding this preflop if the blinds aren't especially bad? Looks like a marginal hand anyway and with the gigantic rake it might not even be worth it?!

If there are 2 nits or 1 fish that doesn't 3bet it's autoraise just for mathematical reasons, you win preflop too often and add to that a bit of edge postflop and it's a raise.

Yes, not as a standard. That would be clicking buttons randomly.

Pretty sure you should open this nearly 100% of the time on the button. Biggest consideration to not would be the stack sizes and 3b tendencies. As played with the Q pairing on the river I would probably fire a third barrel, however I would check this on the flop since this flop does contain a lot of draws and would hate to get raised.