The numbers just don't add up, Thruster.
The depreciation is immediate and harsh. Wife owned a Suburban a while ago. It was two years old when we bought it and had depreciated by almost 20k already, very much like her Volvo. Think about it, that means that even if she pays ten THOUSAND dollars in unexpected repairs, she still comes out ahead. And of course, we never had anything anywhere near that. A used vehicle may have a problem, but you perform a mechanical inspection before purchase to make sure there aren't any expensive ones.
Is that funky cup holder really worth $20,000 in real money to you? Because that's basically what your argument comes down to.
If you buy new, buy because you want new and are willing to pay a premium, not because you think you'll save money. That's a fool's errand.