I think you have about 45% equity versus his range. If you're willing to gamble, I'd get it in. Personally I would 3bet / GII on flop

We still have fold equity with the flop raise. A lot of people interpret a donk bet as weakness and raise often. Villain might be thinking "How many times would he lead a J here?", and the answer would be not too often... So he could raise with a decent chunk of hands to blow you off the pot... If we get the money in, no big deal! It would be a flip a decent chunk of the time

x/c x/c x/f line wouldn't be too bad either I suppose but I prefer to pile on the pressure

Why did you lead the flop here out of interest?

I much prefer having this sort of hand in my check call or check raise range on the flop , i don't like donking with it much. If your going to check raise some semi bluffs you couldn't really ask for better spots to do it in. Id much prefer donking with some bare FD's and made hands.

x/c x/c x/f is a standard line here. It sucks to have such a nice draw when the board is paired.

With how much fold equity you expect to have, and there are a number of worse draws, getting it in can't be bad though.

As played, leading out is fine if you want to induce him to raise and we can come back over the top. I think you took the worst of the options by calling OOP in a now bloated pot.