A pilot with a new commercial certificate is excited at the new world of getting-paid-to-fly they have opened up. That is, until their instructor or good friend reminds them of 14 CFR 119 and the grey line that separates operations that do or do not require an operating certificate.
It is cut and dry that a commercial pilot can be paid to do certain things, but when you decide you are going to start doing things for a friend ("yea, I can transport XYZ for you on my next trip to Kalamazoo") things start to get murky. Especially once your friend starts paying you, you make a habit of transporting things and he tells his friends about your service.
At what point are you holding out your services to the public and when do you cross the line from private carriage into common carriage? How far can you go without an operating certificate.
I'm looking for regulatory answers or anything written from a FSDO, basically anything not anecdotal.
