I came from a transportation logistics background before I decided to
become a pilot myself. I worked in an office, but I am somewhat familiar of
the kind of money an owner-operator can make. I want to make one thing very
clear. Even though trucking and aviation are under the DOT umbrella, the
two are VERY different. During a flight instructor’s first two years,
income is between $25-$35k at the most. $40 if you get help from a Regional
to repay your loan. More info on that can be found on ATP’s website. That
is significantly less than a first year driver making double. I know there
is a difference between intrastate and long haul pay, but still…if this
is really what you want to do you need to prepare yourself for reality.
After a flight instructor has flown enough hours to become eligible to fly
for a regional airline, pay increases to $40-$50k. After about 4-5 years at
a regional, pay jumps jumps well above 6 figures at a major.
Unfortunately I can not tell you if this would be a good move for you. You
either want to do it or you don’t. Same for flying airliners vs
helicopters. Fly whichever one you want. I don’t have a lot of knowledge
about helicopters except that helicopter training typically costs more than
airplane flight training.