Uber for Cessna

This already exists. It’s called Skyüber. It is not affiliated with Uber. However, it hardly has any flights, and is not at all consistent in offerings.

A similar app could focus only on specific markets. A more targeted approach could provide a stronger launch point.

A concern is the highly regulated flight industry. I imaging there is a real possibility this is not allowed. However, I believe regulations are looser around light aircraft.