Here is some research I did Friday on holding out:
Just asking a friend if they want to go to a breakfast if they split the cost is probably not holding out. Asking 10 friends might be. 5 friends? I don't know. It's going to be fact-specific.
If my buddy with a house on Martha's Vineyard keeps telling me we should go for a weekend, and I finally say yes adding that I will fly him and we will split the cost, then I think clearly that is not holding out.
If I ask him if he wants to fly with me to Cape Cod and split the costs when he wasn't originally planning on going, and he agrees, I think that would be OK.
The situation to be avoided is to not hold oneself out to the public as being willing to transport them or their property for compensation.
61.113 is specifically designed as an exception to the rule that a private pilot cannot receive compensation for flying. In that event, the common purpose test must be met. There are letter rulings setting forth acceptable situations.
Mills
Stating that holding out was a fact-specific determination, and that holding out is holding out to the general public at large.
Haberkorn
The holding out can be accomplished by any "means which communicates to the public that a transportation service is indiscriminately available" . . . There may also be a holding out without advertising, where a reputation to serve all is sufficient to constitute an offer to carry all customers. Whether or not the holding generates little success is not a factor
This includes the public at large or a segment of the public, like Facebook friends. Asking a friend to go on a trip, then, may not be telling a segment of the public that transportation services are indiscriminately available.
See the Article,
Come Fly with Me, in the Sept/OCt 2010 issue of FAA Safety Briefing, mentioned in Haberkorn.
This doesn’t mean that you can’t ask people to fly with you and share some of the costs, but the sole purpose of your flight can’t be just to transport your passengers from one point
to another. Asking your flying buddies if they want to split the costs of flying to Oshkosh with you and flying with friends to that resort on the coast you’re all going to share and sharing the flying costs—those would be okay. However, sharing expenses with a passenger on a flight to a place you would not otherwise be flying to would be a problem.
Hold the Line on Holding Out
“Holding out” can be as complex as publishing a flight schedule for a major airline or as simple as posting a notice on an FBO bulletin board (or the Internet) telling everyone you’re the one who will fly them to that prime vacation resort and make their dreams come true. Many FAA inspectors also like to fly for pleasure, and they read those bulletin boards, too. They might not be too happy with your advertisement for Old Bessie’s “charter service” when they find out you don’t have a part 135 certificate, but at least they won’t take you to task for promising to make your prospective client’s dreams come true.
Many pilots believe that they can easily avoid the compensation or hire restrictions of the regulations by making other arrangements. The FAA, however, interprets “compensation” very broadly. For example, the FAA has long held that logging flight time for the conduct of a flight is compensation. Most of us, and especially those of us seeking that coveted left seat at a major air carrier, know how valuable flight time can be. So, if someone requests that you use your superior piloting skills to take them to that resort of their choice and you decline any monetary payment, but still log that flight time while not paying the costs of operating the aircraft, you’ve received compensation.
Goodwill obtained from providing a flight has also been determined to be compensation. Everyone knows how valuable a favorable news article or celebrity endorsement can be. Bartering can be considered compensation, too. You may want to think twice before you take someone flying in exchange for spending a weekend at their beach house.
Knee
where a private pilot develops a reputation that he or she is willing to serve anyone from the general public, then the actions or conduct utilized by the individual to develop this reputation would constitute "holding out.” Actions or conduct which rise to this level would be prohibited solicitation, and hence, operating expense sharing would be inappropriate.