After reading the story on the FP, I have questions. Like, would you be obligated to maintain the road? What happens if you don’t? Would it even be legal to charge for parking on the street? Would that cover maintenance costs, if you had no other roads/equipment for road maintenance?

I have to assume if you own a street in a residential zone, you wouldn’t be allowed to just let it go to shit. There’s obviously got to be good reasons why streets aren’t generally privately owned.