Here's the breakdown.
New car = lots of money for real fun(BMW), or you could buy a kia for the same price as a 90-95 bmw with round 100k mi.
Money for a new car goes into monthly payments and a hefty downpayment, usually. Everything's fixed for free, and usually stays that way because you're paying monthly to drive the car, and can't afford modifications.
Used Car: High mileage, but on a well engineered vehicle, it doesn't matter. Driven hard possibly, but I've driven all of my vehicles hard, for a while. The Bavaria had 488k miles on it, and I street raced it still. No problems, had to replace the clutch once, tho, cuz I learned to drive on it.
93 318i, 113k miles, previously had a supercharger. Driven hard still. 8000 USD flat for it. Only problems thus far have been things like sunroof tilt mechanism and the standard upkeep. If you want your car to be on like-new condition entirely, then you have to shell out anywhere from no where near to much much more than you would pay for a new car, in a non-scheduled fashion. IE, things break when they break, not monthly.
My car runs like a dream, and I can live without a tilted sunroof, thankyou. it still goes in and out. that's all I care about.
End game? Depends on how you shop. Some cars last longer, and last better, than others. BMW has done a fine job of making long lasting, gorgeous, well performing vehicles. So what if it's from last century.. it's class, not kia.