I believe the car featured in the "Flashback" episode was a 1936 Alfa-Romeo 2900MM Corsa Spider. Although Ferrari was founded in 1929, the company didn't start producing it's own vehicles until 1947. Prior to that, Ferrari customized Alfa-Romeos for racing.
In the early 2000's, Brandon was driving a silver Mercedes-Benz SUV. He then switched to a black-on-black mini cooper. He then sold it through the Make Yourself Foundation for charity a few weeks ago. Now I don't know which car he drives.