I dunno guys, I think I win; not for my planning, but thanks to fate.
Bought a Honda Fit, base model (no air, no power locks, unfortunately and not terribly a lot of fun!) but it's stable, it's simple, and it'll never die! $9500, when it was assessed approximately $13,500. That was November 2018.
Fast forward to July 2020, we saw a typical hail storm for the area; alas finally after 6 years of living here, my car finally got hit. Great news though, unlike other vehicles or other storms this produced the most consistent small hail in years. Since the car is a uni-body design including roof, there was no point in repairing things, so it was a full write off to the tune of $7000. After some negotiation, that became $8300.
My $1200 car now has 53K Miles on it, and has a few golf ball dimples in the hood and roof. Barely noticeable, hasn't harmed the paint and (so to the work of Spalding's golf ball design) supposedly is a faster car for it. It's going to drive for many many years to come...