Should airplane ride-sharing be legal?

Cost sharing regulations

Interpretations

How does the FAA find out what’s actually going on anyway?

If I fly somebody somewhere, paying $1 for my share of the costs and the other guy(s) pay the rest, how does the FAA know that? Are there specific record-keeping requirements? What prevents this sort of stuff from happening completely under-the-table?

Likewise with people who hooked up on a fly-sharing web site. How does the FAA even know that it happened?

Because the fly-sharing website needs to be public knowledge to work therefore it can’t be secret.

Sure they can. If I sell you something on Craigslist, nobody has any way of knowing (yet) whether I ever actually sold the offered product, or to whom I sold, or for how much.

It differs because a website charging a fee is not the equivalent of the bulletin board in the student union. A website charging a fee is the equivalent of an ad in the newspaper. Something is the equivalent of a notice on the bulletin board- maybe an individual pilot posting his/her planned flights on a Facebook page or even his or her own website- but not this.

You should also remember a small airplane is not a car. Well it is but its not like a comfortable car with bucket seats and a large trunk. It’s closer to being a small compact with very little room for luggage. They are noisy, claustrophobic, can cause air sickness, and no bathrooms. Can your passengers handle a 2 hour flight like that?

And the thing is with small airplanes, alot is based on weight. You might not want a 300 pound passenger who might not barely be able to fit into the front seat let alone the back. But if one shows up holding his money can you tell him no?

I have never asked a passenger to pay anything for flying with me and while I would cost share with close friends as per the rules, I would never consider taking a paying stranger, nor even a non-paying stranger unless it was something like a Young Eagles event.

The problem as I see it is intent. Is the purpose of the flight because you are going there anyway, or that you are going there because you have paying customers that makes it now worthwhile for you to pick up the smaller cost (or manulip the system to make a few $'S).

And that’s where the law fails this time and every time, it can never regulate intent, only observable actions which are so blurry at times as to create such situations as this.

In any dealings with the FAA it’s important to remember that it’s a lot more totalitarian than almost any other area of US law or regulation.

Absolutely everything associated with flight is utterly prohibited until and unless the FAA describes the specific ways in which it isn’t prohibited. And then you can operate more or less freely within whatever amount of latitude the regulations supply.

Note also that because everything is so tightly controlled, a lot of constraints are implicit. If surrounding circumstances in technology Y or practice Z indirectly affect Rule X, you won’t find commentary in X about what to do if Y or Z changes. The assumption is Y or Z won’t change. Or more precisely, Y and Z are both prohibited from changing without explicit rulemaking.
In this OP’s case we’re dealing with the reality that ride sharing / cost sharing was just barely permitted under the existing regs under strictly controlled conditions. And one of those implicit conditions was that folks weren’t using a world-wide megaphone to broadcast the availability of ride-sharing opportunities.

Because the FAA doesn’t regulate the operation of the internet, they can’t prohibit the megaphone from existing. But they sure can prohibit pilots or aircraft owners using it to advertise ride-sharing opportunities. Or more precisely, such advertising was prohibited before it was invented. Just like all other innovations in aviation.