That was actually my parents. They made good money and pretty much paid to have people handle everything for them. On one hand, it seems like a pretty good life when you don't have to worry about shit and have the money to cover that, on the other, in an emergency, you're dependent on someone else to show up and help.
I had to teach myself from the ground up how to maintain my own stuff. Shoot, we barely had any tools at home, and one of the first things I bought myself when I got a job was a craftsman 200 piece toolset. My parents couldn't understand why I'd spend all my money on it. I'd probably be an interesting case study in nurture vs nature since my parents were basically useless in that regard, but I had grandparents, cousins, uncles, etc. who were mechanically inclined.
When I got older, I spent time fixing my parent's stuff to help them out.
Side conversation: it also feels like the people my parents paid to work on things for them got less and less reliable as time went on. There was one point when I was trying to figure out exhaust on my jeep that my mom offered as a birthday present or something to pay for an exhaust shop to do it for me. I started thinking about it, and I realized I didn't trust anyone locally to do a good job since I was also going to have to trust them to drop the skid plate and properly support the trans and t-case while they performed the work.