I think two ways to go here for me OOP. If I think CO will cbet most times, I can go for a check-raise flop but that isn't always the case multiway.
I think betting out bigger on the flop would be good here, nearly pot size on that texture 3-handed, lots of hands can call that board including overpairs and draws, so we don't want to make it cheap for them imo.

After that it's just cooler time imo, nh, reload, move on.

I don't mind leading the flop here, as a check raise multiway might look pretty strong and some people can't help but believe all donks are FOS. If you do though I'd go bigger, make it look like you want a fold and hopefully the reg with overpairs or a decent draw will raise.

As played, unlucky, no way you can ever not lose the stack there.

Love the lead on the flop but would like it to be bigger. With so many draws out there that's aren't folding you're not going to induce many more folding by using a bigger size.

Turn looks standard, AA is all we're worried about as he will usually stack 99 on the flop. Also A8 A9 might be played like this if he puts you on a draw after donking the flop.

Like the lead. I would be ok with a checkraise too if you expect villain to cbet a lot. I would definitely be going for a larger sizing though. As a general rule, the more coordinated the board is the larger you want to bet. I would be betting at least 3/4 pot on the flop.

Turn of course this time he hit but on average you'll be winning his stack an absurd amount of the time. He can have a bunch of worse hands including top pairs, 2-pairs, the worse set, as well as both flush and straight draws. Definitely get it in and feel really good about it.