There are two schools of thought on what A/C to focus on. Some think it's smart to get a Citation rating since there are TONS of them flying which means lots of jobs plus school is relatively inexspensive. But there are also a TON of Citation drivers looking for work that you'll be competing with. Another idea is to focus on a newer A/C like a GV or CL300 since there aren't alot of pilots with much experience in those A/C... yet. You can charge a premium (I think GV SIC's charge $800-1200/day in my neighborhood) but the cost of school is outrageous.
Real world example: I fly an Astra. 12-18 months ago there was a shortage of Astra drivers in my area. I could pretty much pick up a trip whenever I felt like flying. I charged $450-500/day plus expenses for SIC. It was GREAT. My boss at my PT91 gig pays for all my training and I have his permission to fly all the trips I care to do. On the advice of my accountant I recently started my own "Pilot Services" LLC to gain some extra tax write-offs. I don't know if I'd be able to support myself solely as a contract pilot but it's a great way to make some extra cash.
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