I was brought up to 1) live below my means and 2) if you can't pay cash, you don't get to buy it. The house, of course, isn't in the 2nd category. Being in software in the aerospace industry can be "interesting". I also have a very low threshold of boredom. When my sole responsibility at work is twiddling my thumbs and billing time, I leave. I've been thru 7 companies either went out of business (including 2 major computer companies) or were gobbled up. I left Exxon, Raytheon & ULA of my own volition, I was bored out of my mind. Teaching at the university, has been my most consistent job (20+ years as adjunct). Hence when I don't have a steady engineering job, I can still afford the cherokee. One part-time semester at the university pays for the cherokee - hangar, insurance and annual for the entire year.
I paid the house off in 7 years (of a 30 yr mortgage; I'm a very expensive engineer when working), and paid 50% of the airplane in cash back in 2000 with my original partner. When partner died (not in the airplane, medical issues), I paid off the rest of the cherokee, so I have no long-term debt, only the regular monthly bills. The most expensive monthly bill I have is the hangar rent altho the HOA at the house is rapidly coming close.
Do I want a faster airplane? Of course, most of us do. But I don't need it. If I'm going more than 750 miles, I'm flying commercial. It's faster, cheaper and lots safer (I have no illusions) because I'm not instrument rated.