People Systematically Buying Older Cars

I recently thought about buying a 1990s Jeep Cherokee. They're a simple 4x4 car with a reliable engine and transmission. The engines and transmissions can be rebuilt, so they're viable "forever" cars. I started scanning different web sites for rust free ones. The prices are ridiculous, but they're all selling. It's about $10k minimum for a decent example. I imagine by the time it's brought up to daily driver level, the all in cost is closer to $20k.

To me that seems insane, but when I look at newer model used truck prices, I see why it's happening. A high mileage, 10+ year old Tacoma is listing for around $20k. It will have similar problems to an even older Jeep and require multiple thousands of repairs, potentially, to bring it to daily driver reliability.

When you compare those vehicles to a new truck, though, the $20k is a significant "savings" versus a new car. The average new car "price" is about $50,000 today. Most people are making a $700+ payment every month--for their entire life!--to go from A to B. The used car is likely to appreciate in price (not value) as the dollar is obliterated while the new car is a guaranteed loss of several tens of thousands of dollars. The used car is still pretty expensive to own and operate but it's probably 50% or less per trip versus a new car. 

The entire society is slowly shifting away from the trash that control the economy and government. I think the managerial/financial economy is in its first stages of failure and replacement. I see first hand, day to day, that it doesn't work. It's a good question why anyone should work for it.