Clueless questions
I don't know if it is still true, but I thought there was one manufacturer, could be Tower, that built a trainer that they would replace if it was destroyed while learning with a club instructor. Even if it isn't the most highly recommended plane, I would think that would be a good option, so you don't put him in the position of potentially losing a $100 or more plane while learning. Once he has learned, he could even unload it on Ebay and probably get back more than half the cost of the plane. Just something else to look in to.