Plenty of leasebacks work, you only hear about the ones that didn't.

It sounds like he has the proper expectations financially, but what about
enjoying the plane and liability?

With 3 owners you are likely to be either using it too much to get much
rent, or not getting enough time to enjoy it yourselves. Not insuring makes
it likely to be profitable at low rental amounts, but...

With no liability, how are you planning to protect your assets from when
someone else flies it in to a school bus?