There is no "common interest" here. If you happened to be going on a flight and he wanted to hop along and you agree to a pro rata, then that's okay. But in your scenario, he initiated the flight, and you are being compensated. The Chief Counsel has a very broad definition of "compenstaion". There are also plenty of legal interpretations available to you from their office.

Refrain from doing anything that involves an exchange of money or anything of value (including flight time) with people/businesses while holding a private pilot certificate.

Part 119 says aerial photography does not fall under 135. The OP's idea is a big no-no. Compensation to a private pilot for something he would not have been doing otherwise.

Makes sense, and I understand why they say that a pilot cannot pay less than his share in any case. But one thing that has me baffled is, how the heck would they ever knew how much every one payed?

I don't understand how a tally is kept on that. Is it just a rule that is supposed to be followed in good will?

Have you ever heard of the saying, "we're all friends until we're not"?

When it comes to legalities, your best bet is either not play, or document. I'll give you an example. Boy dates girl. Boy takes girl on flight to romantic bed and breakfast for the weekend via Cessna 172. Girl suggests boy pays room, girl pays airplane.

Months later...

Boy cheats on girl. Girl executes the "hell hath no fury" on boy. Brings airplane rental receipt to FSDO with credit card statement.

You're done.

We're all friends...until we're not.

Gotcha. Thanks for the clarification.

I think that we are all agreeing that this is a commercial operation, for which a commercial pilot's certificate is required, but not a 135 operation.

Exception would be if the pilot paid ALL expenses, or the other party heard that the pilot was planning to make the flight anyway, and volunteered to come along and share expenses.

Joe

Not legal in the FAA' seyes. This is a private, not a commercial pilot. A private pilot cna share expenses, but under a very, very long line of Chief Counsel and NTSB decisions, in order to share expenses, the purpose of the flight needs to be shared. That means, at the very least, that the reason for flying and the destination must be the pilot's.

The scenario makes it clear that the reason for the flight is the passenger's. not the pilot's. IOW, the pilot was not going to go up and the air and fly over a bunch of properties anyway and the salesman just happened to come along.

The short answer is just get your CFI's man. If you do this and you are caught your career is over.

shor answer
 

tell him to get a Drone and a go-Pro and have at it....or you get the commercial ticket.

CaptainRJ

I have a feeling you've had the hell hath no fury scenario happen to you once or twice!!

Back on track....Get your commercial ticket, if you gotta ask questions like these, more than likely your answer will be no, or don't do it.

Think wisely.