Flop: I don't understand check-raising here at all. He folds all of his pure bluffs, continues with everything better, and can sometimes 3bet big semi-bluff type hands, leaving us having to fold the best hand. Just seems like we're bloating the pot OOP with a good SDV hand on a board that is only going to get worse for our hand. Yuck. Check-calling seems far better, with plans to continue on good turns.

Turn: I suppose betting is okay? He's obviously got draws we get value from, but I'd say we're also value-cutting ourselves here a heck of a lot. I'm a bit meh about betting, because we should never get here this way in the first place.

River: I'm super confused now. He's calling with nothing we're beating, and only folding stuff that missed? If you're reasoning for check/raising flop and betting turn was to protect against stuff that had equity, wouldn't we want to check/call vs all the stuff that missed? You're basically turning a hand with good SDV into a complete bluff here for some reason.

Pre: Standard.

Flop: I don't like check raising here, it bloats the pot massively with a fairly weak hand when we are OOP. We're going to take it down quite often with this raise but it makes the hand incredibly tricky to play on so many runouts when villain does continue.

Turn: As played, I think I continue betting here to extract value from his flush draws. We can't check fold I feel so by betting here we get to set our own price for getting to the river. I don't ever expect to get raised here.

River: There are two types of hands I expect to see here, flush draws and stronger pocket pairs to us. By overbetting we are probably going to fold out all PP's that are not AA/KK/QQ and any size bet will fold out his flush draws that do not include a Q. I think the overbet is absolute overkill here and not necessary, I think we can accomplish the exact same job with a smaller bet here, in the region of $5 as 88-JJ will struggle to cal here anyway. We are risking far too much to pick up too little here IMO.

Don't like check/raising flop.
After taking this line, turn bet is a must.

Hate river shoving. I would check/call river. Let him bluff his missed flush draw or Ax.

Spew spewwwww

Absolutely no reason to bluff with showdown value here. It's made even worse by you thinking he hasn't hit this board when a standard BTN opening range can have everything which connects here.

I guess once we play this line betting the turn becomes a must but the river is going to be an awkward spot.

On the river I don't expect him to show up with many Qx so firing again would be consistent but as stated above there's no need to make it so big. All you're doing is to make the success rate needed that much higher.

The usual way to construct your OOP flop bluff raise range is to choose combos which give you a lot of favourable turn cards to barrel. 77 only has two cards you're happy to see. Something like Ad6d which has no showdown value but turns nicely possibly more than 1/3 of the time would be great.