If you have a track record of owning pressurized aircraft with turbine engines, you’re ahead of the game. To begin, you might start out with a used jet. Eventually, you may want a newer jet with better system integration and lower maintenance costs, or at least an avionics upgrade for your used jet to ease the pilot workload.
As for financing, if you have a history of owning aircraft, it helps lenders get comfortable making a lending decision by showing them you understand how to own and maintain sophisticated equipment. Most people with prior ownership understand what they can and can’t manage.
Just keeping up with scheduled maintenance can be confusing. If you plan to make a huge jump in aircraft models and have limited ownership experience, you may want your jet professionally managed. Otherwise management may be too overwhelming for you.
What poses the greatest challenge in moving up is “skipping a step” in piloting skills. For example, going from a Cessna 172 directly to a turboprop is a big jump. More capable aircraft have systems you may never have managed before, such as complex avionics, retractable gear, pressurization, two engines, and much greater speed. This type of transition is not only challenging from a piloting standpoint, but also from a cost perspective. The one exception to this is Cirrus airplanes, where owners can safely transition from a piston-engine SR22 to the single-turbine-engine Vision Jet. Cirrus has gone above and beyond in recognizing that this challenge is significant and has therefore invested many resources to training.
AOPA Finance representatives can help you figure out if a jet is in your future.