First of all I don't think you should be so afraid to squeeze but I guess flatting is ok too, just remember you're going to be playing OOP to one of them post flop.
On the flop leading is good and I like your sizing. Remember he could have a lot of suited connectors and draws (even though you are blocking some of them so that's a good argument for folding) calling preflop because you gave him a very good price to call IP because of flatting and the SB 3x-ed OOP so the CO is getting 3 to 1 to call pre. Also his sizing is almost a minraise so I'm not folding this flop, call flop and check turn to him and see what he does from there.

I think this is perfect Pwll

Squeezing is fine because even though you're not expecting to be able to stack off profitably vs these guys, they do have enough worse hands in their range to be able to make money post flop when they defend by calling. I think given the wacky bet sizes squeezing is what I'd probably do, but calling is fine too.

The flop lead is super standard, you don't expect to get bluff raised by a nit in a multiway pot, and there's no way he is folding JJ,Tx or a draw. If the flop gets checked around it's a disaster. When he raises I would fold because of the multiway factor. If he has a draw his equity is good so we don't really make much by sticking around for a difficult turn.

WP

Ok fair enough, thanks as always guys.