As for your interest in becoming a Contract Pilot, there are a number of considerations. First of all, it is necessary to define a "contract pilot." There are two kinds:
(1) The unemployed pilot, coasting in contract work, relying on their last training date with their previous employer for currency, who is actively looking for a new job (we'll call them the "LOOKER"); and then there is . . .
(2) The dedicated, independent, contract pilot who is committed to contract employment and maintains all their own training and currency requirements (we'll call them the "CONTRACT GUY") Please pardon any reference herein to "him, his, etc., no references to gender intended.
The LOOKER usually does not last very long in the contract business, because they are accustomed to a steady paycheck, benefits, and the security of a JOB. On the other side, the CONTRACT GUY lives and breathes the challenge of his own business, the personal freedom that comes with being a business owner, and has the discipline to budget himself through the good times and the bad times. And believe me, both times exist.
The CONTRACT GUY is also a person who can swallow their ego easily, as usually he is second fiddle, often is not allowed to "fly" the aircraft (gear up and shut up), and is called upon for the worst parts of a trip. Sometimes operators even wonder "what's wrong with this guy that he can't find a job?" -- not realizing fully that we CHOOSE to do this instead of having a job!
Then, of course, there is the annual overhead of paying for your training costs. This is the number one expense to being a true CONTRACT GUY, and separates the men from the boys. A full service Gulfstream GIV / G-1159 training contract will run around $25,000 to $30,000 per year including airfare, hotel and meals during training. I don't know the costs of smaller aircraft training contracts.
There are not a lot of us out there that have the guts to ante up that kind of money to be CONTRACT GUYS. But then we are different kind of people and have different values than most pilots, and the biggest value is our personal freedom.
So if you have the urge to be a Contract Pilot and have the stamina to last out the lean times, then by all means go for it. Hope this helps you think about the prospect. Good luck and stay in touch.
SiBeck Pilot Services
Gulfstream GII / GIII / GIV / GV