I am this person, and 100% agree. My parents are not car people. They provided me with a good education and a solid foundation in financial responsibility, but I have always earned my own way (including my first car at 16). I'm now 34 and have had 30 cars, from the MS P85 to new Range Rovers, Porsche 911s, Mercedes SL65 AMG, etc. I'm now at the point where everything is "been there, done that." If I could go back and do it all over again, I would've drastically slowed down my pace of car flipping and would probably have another $250K in the bank. I've made money on a few, lost on most, and overall spent way too much on cars than I should have...and now it's kind of boring. The "hunt" for exactly what I wanted is no longer very exciting. For someone as passionate and obsessed with cars as I am, it's much more fun to have something to look forward to and strive for rather than being at the top so early. It keeps you hungry and pushing to get to the next level. I'd much rather be saying this at 64 than 34, and can't even imagine having to pay for a Model S right out of college.