I try to avoid doing insurance checkout for private pilots on their new to them airplanes. The problem is that I usually find multiple areas of poor flying skills, so it isn’t a checkout it is basic flight instruction because I am not going to sign off on anyone without good aircraft control and I am not really interested in doing basic instruction anymore.
Most of my insurance checkouts are for low end warbirds, like Nanchangs, Yaks and type ratting training for T28’s.
I have a structured 10 hour course starting with a full day ground school and I am a known quantity for the insurance brokers that deal with these kinds of aircraft.