Those look like very significant savings to me. And what does "Win" mean? As far as safety goes I agree a 2017 corolla is demonstrably better than a 2000 one.

A 2010 Corolla will save you $10000 over a 2017 one.

My core premise is most new cars are of much better quality than those from 20+ years ago when it made sense to buy new because that 36k warranty and 60k power train warranty was critical. These days most cars will not fail that early unless it is on petty cosmetic things.

My wife had a 1999 Corolla that made it > 300000 miles on it. IIRC all she did was oil changes and occasional maintenance like brakes. The biggest repair I was involved with was when the starter motor wire shorted to the chassis and burned up the wiring harness. That would have been an expensive repair to do "right" by pulling the entire harness but I instead replaced the wires with burned insulation one by one with correct gauge soldered and shrink wrapped and as far as I know is still alive and well with a relative. I think the repair cost me a few $100 but that car had no major work done over its life span AFAIK. There's my anecdata...