Hello all, Firstly, this is a conversation that needs to be had with my insurance. Before I do that, any personal guidance and experiences are appreciated. Situation: I have been debating purchasing a tailwheel airplane (champ, tcraft, luscombe, etc). I am a CFI. My goal is to provide instruction in the airplane and allow my students to rent it from me, solo it, and fly it if they choose after earning their certificates. Other non-students would be able to rent it from me also after a checkout. A good friend is an AP/IA so annuals and 100hrs will cost me parts, not labor. This would not my main source of income. One of the largest fixed expenses in insurance, hence the reason of this post. Looking for any insight from those CFIs or other pilots who have come across a similar situation; a CFI providing the airplane and charging for the plane and instruction. Seems that flight school insurance or non-equity flying club insurance is what is needed...any advice on questions to ask, things to consider, or personal experiences is appreciated. Thank you!