Bad economies and a lack of available work often spawn a surge in owner operator jobs and entrepreneurial ventures. If you are currently experiencing the crunch of expiring unemployment benefits and no work to be had, you may be willing to start your own business too. Here are a few owner/operator jobs in the transportation sector you can start as a one-person operation.
Boat charters are very popular on coastal waters as well as large inland lakes and rivers. As long as you do not require a deckhand's help to keep your boat afloat and keep it moving, you can buy a boat, a charter license, and rent some dock space to get started. If you also buy a boat with a cabin below, then you can live on your boat if and when times get really tough.
Ferry service is similar to boat charters with the exception that you are operating a much larger craft and you can opt to transport cars and trucks across lakes and rivers. Your biggest competition is the city-owned and operated ferries, but as a private ferry charter you may find that you have more customers when you offer a service that the city's ferries do not. For example, ferries in one of the largest cities in Newfoundland and Labrador, Canada, do not transport vehicles. A private ferry that does would definitely profit. Ergo, all you have to do is find out what services are not offered by the ferries in your city, and offer those on your ferry.
Black Car Service
While many travelers can grab a taxi at the airport, many would prefer to travel in style instead. You would have to invest in a black luxury sedan of some sort (e.g., Cadillac, Lexus, etc.), and then spend your days parked in front of the airport waiting for fares. You will either have to install a fare meter, or establish a pricing system for fifty of the most popular destinations within your city. It may also help to invest in a very nice chauffeur's suit and/or something else that would signal that you are a black car service. You could use magnetic signs on the side of the car, which are removable once you pick up a fare, but generally it looks a little cheesy, so you will have to figure out how to best advertise your services while you are waiting.