Winguru. If the owner has enough money to buy a personal T-Prop, than he or she has enough money to do the training properly. As I understand from your first post the owner allready has an FAA PPL and wants to do the IR and type training. All the insurance issues go away if you send the high time guy you want to do the instruction to SIMCOM or FS to do the Type course, pay for 10 hours or so of LOE for him with a instructor with lots of time on type and then he can start the training of the PPL. For this catagory of aircraft proper type training, including simulator training, is not optional, if you are to truely understand the aircraft and how to properly fly it.