By 10+ years old on that car, I was starting to have to do non-zero-cost maintenance (above oil change, etc), so having a newer car will remove those costs (and annoyances) at the cost of a bit more up front now. Small, calculated tradeoffs, I guess.
But in the discussion with the guy I referenced above, he's... a car salesman. Part time. But he's sold enough that he can 'borrow' any car he wants, and constantly rotates through phenomenally nice/upscale cars. He has a hard time imagining have to go back to driving 'dumpy, low-end' cars like my Focus. I have a hard time imagining going back to 'check to check' living and always being behind on bills. He's not necessarily in that situation, but I know him well enough to know he doesn't have 3 years of expenses saved up.
My current car is old enough to vote. But maintenance is cheap and its comfortable to drive. Why would I buy a newer and more expensive car?