He who dies with the most toys - wins.
Good buddy lived this way. He eventually sold all the cars, boats, wave runners, camper, lake house, etc. He STILL has the $50K(?) Camaro - with $7K after market blower - 800HP(?).
He is in debt half a million at age 76. BUT he still has good SS and some pension (DW also has these). SO, he typically can meet his payments and live in a nice (not fabulous) house. He scrimps ONLY when he has to. Technically he owns nothing but the cr*p INSIDE his house.
I'm not certain I can fault him, but I'd be dead if I'd had his stress level. We both w*rked at the same place and made about the same money. Between he and his wife, he had about the same income as DW and I. Occasionally, I sense his envy of me. He knows (in general terms) that my paid-for condo is worth more than he owes. He never protests that I pay whenever we go out for lunch, etc.
I guess the two of us are just about perfect opposites as defined by this thread. Still, we are good friends and always have a good time together - especially reliving HIS past. YMMV