My first car was $800 and I bought a few motorcycles over the years for around $400 each.
It blew me away when I got that Scion. It was a steal of a deal. I was looking at used, late 90s model Civics at the time, because I needed a commuter that could do 50 miles one way with decent MPG and with something I knew that I could keep on the road, and those cars held their value so well into the late 2000s that it blew me away. People were asking $3,000-$4,000 for them with 150k-200k miles.
Today, I make something crazy like about 15x what I made in 1996, but I still have that Scion. I plan to keep it on the road for another 11 years. After all, it's a Toyota and it's given me no trouble at 150k miles. It goes to the shop for tires, everything else I handle in my garage. It's a commuter for my wife that goes about 5 miles one way these days.
My neighbors comment on it all of the time. They think it's an unsightly beater sitting in front of our ludicrously expensive homes. I thought about selling it for a while but their shitty attitudes have convinced me to keep it around.
There are many examples of people overcoming crazy challenges, makes for a nice story but also having a regular/"painless" life is also nice. I did not enjoy riding the Walmart bike that far/many hours. It was nice though the nature aspect.
I still think I am being lazy, not trying hard enough, about being an entrepreneur like did I really try... not drop shipping but building some service. I keep thinking is what I do worth it if it doesn't make money since that's my primary concern right now is getting out. (not be worried if I lose my job) I gotta stop responding haha, wish I could condense my previous posts.
edit: clarification, the car was a bad buy(not a car guy) it was just under $2K so I had a buffer but it was partially broken... so I had to drop money on it.