I don't think there's a right or wrong answer; everyone has their own environment & hot-buttons.
My oldest car is a '68 Road Runner, newest is a modified '97 Mustang GT. There's also the racecar, a daily beater, an SUV, a 4x4 K10 and a Dually.
Kind of a "tool for every job". Or a toy for every mood.
The old stuff arguably has the most personality & soul, but it comes at a price: a bit raw, so to speak, and needing more maintenance.
Newer tech results in better numbers, more comfort & refinement, but a different driving experience.
52 years after my 1st car, I still build cars in my head, and am always tinkering, if not working on a total project.
I'm glad I don't have to limit myself to 1 vehicle, that would drive me nuts.