Pluses and minues to both. It is a tough thing because when you do one, you miss the other. There is something said for getting into something nice everyday like a Golf R/Macan that can do it all well. Sucks when you think you can end up spending the bulk of your time in something meh, while the fun car barely, or rarely, comes out. Isn't life to be enjoyed? Frankly a Macan/M340i/S4/Golf R level of vehicles do everything well.
But it is awesome to have a toy in your garage that comes out only when you want, and when i had a 3 car setup, i loved how driving the average DD made me appreciate the toy so damned much, i never got jaded. Also for a car guy like me, subjecting a great toy to terrible Michigan winters is just depressing, and i loathe parking a nice car where it can be molested.
Ice T said ever man needs a wife, mistress and a hoe. I agree with that.
My favorite setup was a nice toy, a nice DD, and a beater. It covered everything nicely, but when you think about how much you might spend on 2-3 cars and the insurance and upkeep, that pays for a terrific higher-end one car.
Right now i am in one car, and have been that way for years and looking to get back to a multi-car setup now that my divorce is done and i might move to kill off my current massive commute. For instance, my current realistic dream toy is a Supra 3.0, there is no way that could be my only car. But i would rather have a Supra 3.0 and then a DD of some sort over spending the same amount on a well equipped Cayman 4.0.
Truck guys get it easier, Jeeps/trucks can haul stuff, carry multiple people. Sport sedans guy can handle it well, it's the sports car guys that suffer, because nothing drives likes a Miata/Cayman/Supra, and none of those provide sufficient practicality to be a solo car for the majority of folks.