Pilot124,
Of course you can hold out. If you want any business as a flight instructor, or work as a commercially certificated pilot, you realy need to hold out.
Holding out is nothing more than advertising your services. It can be by any means. Word of mouth is holding out. Giving out business cards, passing out flyers, putting an add in the paper, making a banner, all means of holding out.
What you can't do is hold out a willingness to transport persons or property for compensation from one point to another, without a Part 135 Operating Certificate.
Outside of that, you can advertise yourself as an available commercial pilot, and you can certainly advertise yourself for flight instruction.
Now it should be noted that you can be hired for flight instruction and may land at a point other than the point of departure. However, you cannot be hired to fly someone to a point other than the point of departure, if your'e holding out as a transportation service. Providing instuction is fine, selling transportation is not.
You can hold out as a pilot willing to fly people to other destinations in their own aircraft, or aircraft they arrange/provide...but not in aircraft you provide. The intent is to prevent just anybody from setting up their own defacto airline or charter service, without the full oversight of the FAA Administrator.
You can provide the flight instruction, and during the course of the flight instruction you will be landing at other airports than the point of departure. This is legal.
Where the issue of legality would be blurred would be if someone approached you and said, "I hear on the street that you'll fly me and my cat to Hangtown for two hundred dollars if we just call it flight instruction." It would become illegal when you accept and conduct the flight. It's an area where folks have tried to skirt the charter regulation for years by justifying an illegal charter as instruction, forgetting that the FAA is just as interested in the intent and purpose of the flight as the semantics.
If you're providing genuine instruction, you're in great shape. If you're holding out for transportation and calling it instruction, not. If you're not providing the airplane, but are simply providing pilot services on a nonpublic level (Cindy-Lou Freebush wants you to fly her to Dogville in her Twin Bonanza), you can do it. If you're providing the airplane (Cindy-Lou Freebush wants you to fly her to Dogville in your Twin Bonanza, for five hundred bucks), you cannot.
