It is interesting to me that you compare to Lyft, which looks very much like a taxi service to me, whereas Flytenow looks more like a ride sharing bulletin boar

It is interesting to me that you compare to Lyft, which looks very much like a taxi service to me, whereas Flytenow looks more like a ride sharing bulletin board. For what it's worth (IANAL), I agree with their interpretation and would not be worried about it. EDIT: Of course, it is easy to imagine scenarios where a pilot, using this system, could get themselves in trouble. The same could be said, however, of a traditional bulletin board, so the onus is on the pilot to make sure it doesn't look too much like transportation for hire.