You don't even need a $500k net worth to afford a Cessna. Most guys I know that have them are firmly middle class. They have to make some compromises on houses and cars, but it's worth it to them because they love to fly.
Somebody was asking about this on Reddit (/r/flying I think) a few months back. Short answer is that the FAA does not take kindly to receiving payment if you don't have a commercial license, and if you do then there's better work out there than Uber-for-cessnas.
