<i>namely expense sharing as long as the pilot is paying his fair share of the flight expenses</i><p>That&#x27;s not compensation. What he is talking about is two pilots, usually broke pilot students at the same FOB, who have their PPL but need hours for their CFI, IFR or some other type rating. So they share gas and then do different legs as pilot in command, it&#x27;s cheaper, you get your hours and have some company. I can tell you from first hand experience, solo cross-country, is boring as hell. I even did it before GPS was a thing and you have to do IFR landmark based nav - still boring.<p><i>If you mention to your coworkers that you are renting a Cessna to fly to some specific place to visit family over the holidays and a co-worker says they want to go there too the FAA would have no problem with you taking them with you and having them pay their share of the expenses.</i><p>It&#x27;s been a while since I flew, but that was definitely one of the things that was drilled into me as &quot;not legal&quot; behavior for a non-commercial pilot. Your scenarios would bust all 4 common carriage rules. &quot;Goodwill (dropping off clients) is not bona fide purpose (likely is compensation)[1].&quot;<p>[1]<a href="https:&#x2F;&#x2F;www.nbaa.org&#x2F;events&#x2F;amc&#x2F;2011&#x2F;news&#x2F;presentations&#x2F;1011-Tue&#x2F;NBAA2011-1011-1030-Reimbusement-FARs.pdf" rel="nofollow">https:&#x2F;&#x2F;www.nbaa.org&#x2F;events&#x2F;amc&#x2F;2011&#x2F;news&#x2F;presentations&#x2F;1011...</a>