Tim's bit here is ham-fisted as always, but he accidentally stumbles across a relevant point about Portlandia.
The show couldn't be made today, not because it was "anti-woke satire", but because it appeared during a time when liberalism was so secure that it could actually poke fun at itself. Liberals no longer feel that security, so any sort of meaningful introspective humor is forbidden because it might expose their weaknesses to the enemy, or might signal a disunified front.
This is why the bastions of Obama Era comedy (The Daily Show, Colbert, The Office and Parks and Rec actors) are so humorless now. Good comedy is about opening up about vulnerabilities, foibles, inconvenient realities, and exposing them to the air - something which no liberal during Trump 2.0 can afford to do.