I didn't read all this. But are you smart or stupid for driving off a lot with a new car and taking an immediate depreciation hit?
lol Cars are an expense. Anyone who deludes themselves otherwise is stupid. The level to which someone is willing to pay that expense is not necessarily a measure of intelligence but of spending and expense tolerance.
Not only that but circumstances can dictate your decision one way or the other. Last year I bought a brand new Silverado crew cab. Our Maxda CX-9 was old and certainly wasn't going to pull our horse trailer and my '97 F-250 is not reliable enough anymore. We looked for over a year for a used truck that could double as our family car (4 doors), get up our driveway in the winter (4wd) and pull a horse trailer. We didn't have that much cash all at once so financing was necessary. The used trucks we saw that fit our monthly payment all had over 100k miles and no warranty. The new truck had much better financing available then the used trucks so it had lower monthly payments and had a warranty. Yes, we will be paying for the new truck longer but it starts at zero miles instead of over 100k. When I crunched the numbers the used trucks and the new truck ended up with the same miles on them at the end of their loans. So in my case the cheaper used trucks were not cheaper at all and made no sense for us.