Contention: For any dollar amount that you can dedicate to your automobiles, a combination of multiple vehicles that fit within that budget will always win over a single car. If you live somewhere like NYC where your parking is a giant issue and owning two is almost impossible, you don't love cars enough and should move.
From $5,000: a 95 Miata and a 92 Ford 4wd Truck.
to $200,000: a GT-R/ZR-1/Viper and an E63 Wagon.
For any practical given dollar amount, there are always two+ cars that would generate more hoon happiness than a single car. You can always have an unreliable/2-door/RWD/manual tranny/summer-only-tires/track-happy car AND a family/friends/slushbox/foul-weather/tow-vehicle.
If Chump-car has shown me anything (other than that stock V-8s always overheat and your best friends are terrible drivers), its that you can have a sh*t-ton of fun with a cheap-but-impractical car if you have a cheap-but-practical car to use other times.
...AND that some of the best times I ever had on a twisty road were in worn-out manual RWD crap-cans.
Prove me wrong...