Yeah, this is a running joke among certain species of chantards/wrestling nerds. "Such and such's dogs are in the enclosed pool area" is a way of saying "such and such is about to flip out and end it all," "such and such is having a really lousy day right now," that sorta thing.
Unlikely. It's hard to guess what Singal actually believes when he's alone, but I know he believes one thing, which is that the tightrope-walk act he's been working for the last several years has made him a whole lot of money. Legacy media dinosaurs like the Atlantic and the Economist aren't buying articles from anyone who goes full TERF.