I am a member of a local WAI chapter with 501(c)3 status and am looking at fundraising opportunities. I have a friend who owns a tailwheel and want to ask him if he would be willing to donate his time and aircraft hours so we can sell raffle tickets for a tailwheel endorsement. Before asking him, I want to know if it is legal or if there would be any stipulations. Would the better alternative be to pay him our of the funds raised?
If it's legitimate ("bona fide") training, i.e., your friend is an appropriately rated CFI and the person who gets it is a real pilot and it's real training appropriately documented in the pilot's logbook, not a joy ride for a non-pilot, there's no problem for him to donate his time and the use of his airplane at his expense. Otherwise, you need to comply with 14 CFR 91.146 "Passenger-carrying flights for the benefit of a charitable, nonprofit, or community event."