Old classic cars can fetch a lot of money at auctions and most have a lot more style and character than modern cars. However, that style often comes at the price of driveability. Modern electronic engine controls have eliminated such quaint features as manual chokes, vapor lock, flooded carburetors, dysfunctional drum brakes and more.
San Francisco writer Paul Boutin tells the tale of living with a 1963 Studebaker Avanti coupe that he and his wife decided to use as their sole car in place of more recent sedans. The Avanti certainly has style and all those other aforementioned features of old cars, but basic reliability is in desperately short supply. If you're going to have such a car, it would probably be wise to have a solid backup unless you have access to good public transit.