I am currently making my living as a contract pilot. Because of school I am unable to go full time with anyone, so all of my flying is done a daily basis with a few local companies. Obviously school limits the amount of flying I can do, but I still do one or two trips a week. If I really hustled and was willing to travel around the country, I think I could make a pretty decent amount of money. I hate airline travel and I don't like driving, so I normally turn down anything more than 100 miles away.
Finding work isn't too hard right now, but it is not like it was this time last year. Most places have slowed down and there are a lot of quality guys out on the street. Having time in an unusual airplane helps a lot. Right now there is only one Falcon 7X contract pilot. He is charging $3,000 per day and staying busy. I have gotten a few gigs because I was the only one around with time in type. Devoloping a good relationship with the insurance brokers in the area is very important. If they say you need 25 hours dual to be cut lose in a Saratoga, that company probally won't use you.
The big problem with contract work is that it is unpredictable. You will want something to supplement it. For me, that is flight instruction, and by that I do not mean doing stalls in a 152. When an owner buys a new high performance airplane, most will need quite a bit of instruction. Sitting in the right seat of a Saratoga, Baron, Malibu, ect helping the new owner get comfortable flying the airplane is another good way to make money. I developed a reputation at my local airport for helping people learn new airplanes and new avionics, this helped to bring in quite a bit of work.
I formed an LLC to do all of my flying under. I would recommend it as it makes things a little easier. Keeping track of all payments and expenses is also very important.
I have always viewed contract flying as a step to getting a full time job. I would not want to be a contract pilot for my career. I would not leave a stable job to fly contract, especially not in today's climate.
I charge a daily rate of $300 for pistons, $500 for turbines, and $300 for jet SIC, with a discount on turbines if they pay for my annual training.
Let me know if you have any questions,
Alex.