My Father grew up as a farmer son in the depression with little to no money. His first car was a worn out '36 Ford around 1941 after he graduated from high school and started working with a sheet metal shop. In early 1942 he and two friends left North Carolina for the first time to go to Baltimore and work for Glenn L. Martin Co. building B-25 bombers. Drafted in 1943 and sent to Europe as a combat engineer, clearing mind fields and building bridges. He returned in early 1946, studied to be an electrician in NYC and then returned to North Carolina. Back home, he entered a business college for an accounting degree where he met my mom who was one of his teachers. He went on to be CFO of a major east coast hospital system. Shortly after he married Mom in 1950, she wanted a sewing machine. He agreed to buy her one if she promised never to try to make him a shirt. He would have no more homemade shirts.
With that background, I can start to answer the OP's question. Dad enjoyed old (antique) cars, but had no desire to own one. He had too many old and hand-me-down things growing up. However, he always supported me in my interest in old cars. At 14, my grandfather died. Dad said he would get me his 1949 Plymouth. An uncle sold it before we got there to see about getting the car. Dad then said that my Mom's aunt had a 1949 Hudson that we would talk to her about when we went down there the next month. Well, it was sold and gone too. When I got my drivers license at 16, I was given the 1961 Dodge Polara two-door hardtop that Dad bought new and was then Mom's car. It was replaced with a 1968 Dodge Charger for her. After about a month of driving the 1961 Dodge, I told Dad, I think it need a tune up, not knowing if it did or not. His response was, we'll do it. I had no idea he knew how to tune a car. We did it. I was very impressed. When asked what I wanted for a high school graduation present, I said I want one of those big Sears Craftsman tool kits. I got it! Still use them.
The biggest lesson he taught me was to buy the tools you need to do the job right and the next time you do it, it won't cost you anything but parts. I still follow that rule.