Most of my power flying these days is aero towing gliders in Alberta. My club requires a Spring checkout, once the snow has gone. In the case of our current towplane, a Pawnee, that requires another tow pilot observing my landings. 😄
Almost all of my other power flying has been renting from training organizations and so there were dual checkouts.
Two years ago I started flying a friend’s C182. Since I had over 100 hours in 182s, his insurance company only required a flight and some circuits with the owner, who then OK’d me with the insurance company.