This is a perfect demonstration of the divide between people with money who will stay rich and people with money who will go broke eventually.

Wealthy individuals who become poor are irresponsible with their purchases. They buy things to consume conspicuously and show off their wealth to others. They buy new cars, cell phones, and computers even though their old ones function just fine.

Rich people who stay rich are responsible with their money. They don't make purchases that are unnecessary. They save their money and invest it wisely. Just because your family has a generous yearly income doesn't mean that you have to spend it. My wife and I combined make 150k a year straight out of college (not counting bonuses, benefits, or returns on our multiple investments), and I drive a 17-year-old Honda Accord with 200k miles on it. My car is not the best one in the world, but it gets decent gas mileage, and, most importantly, it still takes me from point A to point B every day. I have no plans to replace (even though I definitely have the cash on hand to do so) it as long as it keeps driving me around without any problems.

Methinks you are over exaggerating about how crappy his car actually is. I'm assuming that it looks like a shitbox, but that doesn't mean it isn't a dependable shitbox.

As an aside, how much do you think a new car costs? I can guarantee you from experience that even basic minivans are not cheap. If he needs a large van for his job, prices only go up from there. From a quick search on Carfax, even a decently used Ford van runs around 20k.

You really could learn from your father's experiences. Save your money, invest it wisely, and don't buy shit that you don't need.