When I started back up after 30 yrs., I rented for about six months. I took the family for a quick trip to an airport 63 miles away. The bill for renting a crappy C-172 plus overpriced fuel came to $214. At that moment I knew that I had to get my own plane or stop flying. The owner of the FBO tried to disuade me by telling me that 100/yr was the break even point. Even knowing as little as I did, I knew that a plane would not cost me $11,400/ year to operate. I sold the powerboat and started looking. It took about seven months before I found a low time Warrior for under $30K. Along the way I found a freelance AP/AI. He was invaluable. He helped evaluate candidate aircraft and did the prebuy. He will do an owner assisted annual for $400. Hanger rent, ins., maintenance plus a couple hours of gas runs about $300/month. I never worry about when to get the plane back. When I want to go flying, it is always there. There is no minimum daily charge. I can be gone for weeks at a time and it doesn't matter. But, honestly, I do worry about maintenance but my AP gives me a lot of free wisdom that helps a lot. I did some upgrades to the panel, to work on my IR. But that too can be done for a lot less than conventional wisdom suggests. So far it has worked out. A nice Cherokee can be had for under $20K. Out in the mountains I would suggest a 180 hp., but that is certainly not a requirement. You would be surprised at what can be had for the price of a car. Get something that will burn Mogas.
Plane ownership is certainly doable for the middle class. Find an AP that will work with you. Involve youself in the care and maintenance of your airplane