Beardedflyer,
As far as starting up an operation. There are people who do the one man band kind of thing. Actually that is how my father started out, one airplane, one guy flying it, and yours truely setting up signs. Gradually over the years it has grown into a very lucrative operation with multiple planes, pilots, and ground crew. First off before buying the plane, equipment, and what not, a trip to the local FSDO is in order. You'll need a waiver in order to tow commercially, the guys at the FSDO will be able to outline exactly what is involved. I can't give you exact details because every FSDO has different set of rules, and they don't communicate. Our waiver covers a three state area. It also allows us over flight of stadiums, NASCAR events, state fairs, ect....basically large gatherings. It also outlines, altitudes we are permitted to fly, and general location specific procedures. (We tow over a heavy beach resort area, so the waiver is specific as to which way to turn when we make our climbs, away from the crowds). General details such as those are what the FSDO will help you outline. Next thing will be to get the plane, it will have to be inspected, put on the waiver, then you'll have to demonstrate a pick, tow around the patch and drop for the FAA. They stand on the ground and watch you do it. Keep in mind it will have to also have 100 hr inspections, another cost. As far as equipment, GASSER banners is where we get the red letters from and I don't order that stuff so I can't say for sure what a letter runs right now price wise. We have such a huge inventory we don't order much anymore, and a lot of ours was acquired by scooping up used stuff from smaller operators going out of business. Also finding an airport and getting approval to tow out of it is another step, it's always preferable to have one very short distance to your target area.
As far as clients, I would say areas with large concentrations of people outdoors would be where to start. From there it really depends. We have TONS of restaurants, beach shops, outdoor tour operators, seafood markets, put put golf, go cart tracks, you name it. Anything people can do in a beach town, they advertise. And for those clients, on your down time you'll have to go sell yourself to them, walk in and pitch your sales speech. Once word gets out, and shop owner A see's shop owner B's banner go by on his saturday off, that's how it typically starts to unfold.
to address Crimsons statement that its dangerous. Certainly is. No argument. So is driving down the interstate in the pouring rain at 75 mph with no tread on your tires. Yet people do that every day without a second thought. Like I've said before it's largely as dangerous as you make it. Granted there are operators that don't give a hoot about maintaining the planes and equipment, but there are also those who certainly do. Because at the end of the day, a little money spent on general maintenance can go a long way towards the bottom line. However anyone who is in this industry for any time will soon learn that is everywhere. I've worked for charter companies that fixed write ups ASAP, and those who would rather you limp it along, at some point we will all come across those issues. And you have choices, do it their way, or do it your way. Your way might end up being to move on down the road, nothing wrong with that.
Last note,
As far as worthless time. It's not worthless, it's flight time. Like I said before, I have roughly 2000 hrs towing banners, I am currently flying for an airline. Prior to the airlines and post banner towing, I few Beechjets, MU300s, three different Citations, and Learjets. It's really about the contacts you have, not the type of flight time. Once you get to a regional, and believe me they will hire you with banner time, you build a couple thousand hours and once things start moving again the majors will look at the banner towing as a blip on the resume. That I can attest to based on how many people I work with or know who towed and are currently flying at majors. Contacts is what gets you up the ladder. At our banner company, we have yet to have a pilot not be successful in moving up the ladder. All of them are flying corporate, freight or for the airlines.