My story starts with getting my PPL when I was 17 and loving to fly. I went to College and thought about an aviation career, but to me Engineering was easier - no struggling at the start, just get a job when you graduate. I was fortunate to get a job with McDonnell Douglass making good $ and got married and got my husband a job there too. We talked about building a plane which he really wanted to do, but that never came to be. (Turns out he is afraid of small airplanes). Bought my first airplane a Pitts S-1C when I had enough money to pay cash, but didn't. Got a loan from Bank Votaw (Parents) and keep my $ working for me. Kept that airplane for 10 years, lots of fun, lots of contests, and one engine re-build where the hanger owner where I rented was an A&I and he did most of the work for me. (I just did what he told me to). Sold the airplane after 3 kids and no time to fly, when I could go the the airplane it was more maintenance than flying. I didn't want to be one of those 10 hours a year unsafe pilots, so I stopped (not quit) flying for 10 years. Then the kids were older and in school (I retired to raise my own kids when the oldest was born), my husband was making good $ so started looking for another. Then several life things happened at once. My husband was the one always getting us into credit, always wanted a bigger house, bigger car etc.... So... that was falling apart. Then my Dad died, followed by my Grandfather (Dad's Dad - gave up when Dad died from cancer) and I inherited some money. Bought the CubCrafter S2, and again could have paid for it but financed because it was the better decision. Side note: agreed to do a lease back to someone I originally trusted to appease the soon to be ex. He turned out to be a bad egg and had to get my airplane to safety - think moving it in the middle of the night. He sued me and I had to pay him off. I just consider that to be a cost of the divorce. Sooo anywho before I bought the airplane i re-upped my currency, recertified my CFI and now I teach tailwheel and have the airplane as a business. I don't teach full time (still have a minor at home), but enough to break even for all my flying and get a good tax write off. Side note 2: I had to take the house in the divorce, didn't want it, but with the kids and such it made more sense, big house, big mortgage payment, and that was right before the real estate crash of 2008.... When the ex left, so did all the debt except for the house.
So now I own my own airplane and business and my flying is for free. Worked out for the best.