Thanks guys, a lot of this stuff we did talk about, especially the twin vs single. He actually has considerable twin time although it was mainly "normal" flying and not training flying. IE, all systems worked and no engine failures. He also has considerable instrument time.

The one thing that I did try to sell him on and he agrees is an aircraft with known-ice. They want to be able to fly in the winter time IFR. Obviously I stressed the known-ice in a light single/twin is not to fly IN icing conditions, but to fly THROUGH it and get to clear air and even then it's not always the best practice.

I think the main thing that he would want a twin over a single is just useful load. He said he would want to be able to easily carry himself + 4 pax and some luggage. A 210 might be able to do that while a 310 would be able to do it better.

Thanks for the info regarding insurance and inspections. Again, I know all about how often these inspections are required (teach it to every new student) but didn't know how much they cost.