My two airplanes are both paid for in cash and combined cost less than half a years salary. Annual upkeep on simple airplanes like these is not insignificant but well within my budget (my son's after school tutoring cost more than hangar rental). Yes, there can be some big ticket surprises but insurance helps with that. They both have held their value and I can easily sell them for the original purchase price.
There are a LOT of things that ownership opens up that renting can't give you. First off, nobody else touches much less flies my airplane but me. It's always exactly how I left it a week ago. I don't have to worry about what the last guy did or if the flight school is properly maintaining it. I can go from getting out of my truck to rolling down the runway in 10 minutes and haven't even decided where I want to fly today. These types of planes are not available to rent anywhere so owning is the only way to fly them. Money wise, it's a lot different when the hourly rate is mostly just Avgas (and neither of these are particularly thirsty). Waiting in line for takeoff for 15 minutes is different when it only means 1/4G of gas.
The joy I've gotten out of my planes is worth every penny.