I am preparing to take my Commercial Pilot checkride in a month or two, and I am preparing for the oral. I know a big chunk of the oral is going over what a CPL can do and cannot do (i.e situations concerning if you can legally take a job offer or not). But I am having trouble figuring out a solid way to determine if a job can legally be accepted. I've looked around multiple training resources for situations as well as their answers. But I feel like for some of them, I've read very different answers. It seems like a pretty blurry subject. I'll list some common scenarios I have found throughout my search, and the answer I feel is right from what I have collected, and if I am wrong, please correct me. Feel free to throw some more examples out there, as I really want to grasp an understanding of this subject.
1. A local businessman reaches out to you and asks for you to fly him to a meeting. He will rent the aircraft to be used, and he will pay you. Legal?
In this situation, holding out is not a factor, as the businessman reached out to you (assuming he didn't see an ad, or find out because you have a reputation of doing flights like this). They are providing the airplane, so as far as I see, this falls under private carriage, and it can be done as long as aircraft maintenance requirements are met.
2. A local businessman reaches out to you and asks for you to fly him to a meeting. He asks you to rent the aircraft, and he will reimburse you as well as pay you for the flight. Legal?
In this situation, holding out still isn't a factor. However, he is asking you to provide the aircraft as well as yourself as a pilot, which falls under the scope of requiring an operating certificate because the pilot and aircraft are coming from the same source. So this flight is not legal unless an operating certificate is obtained.
3. Your family reaches out to you and asks if you will fly them to Florida in your aircraft. They will pay you to do so. Legal?
This one is a no, since you will provide the pilot and aircraft, you are essentially acting as an on-demand charter, which would require a 135 cert.
4. You own an aircraft, and want to charge people to give local tours which begin and conclude at one airport. You put up a sign that advertises these tours. Legal?
I'm a bit unsure about this one. Technically, you would be holding out to the public with your sign. But the operation does not fit the definition of common carriage, as it does not go from place to place. I am pretty sure this one is a no, but I am not sure of exactly why. I'm looking in part 119, but I don't believe it is one of the exclusions.
5. A businessman leases an aircraft, and wants you to fly his company employees to meetings. You will be paid for your services, but the employees will not pay for the flights. The company will cover all flight costs. Legal?
With only this information, it can be assumed that holding out is not a factor. The business is providing the aircraft by lease (which from what I have read, in terms of this subject, might as well mean that they own it). Since the aircraft and pilot are not coming from the same source, and the company is not profiting from the flights, this operation is legal, as long as maintenance requirements are complied with (side question; does anybody know where I can find these requirements? part 119?)