If I had a chance to own a mega Ferrari it would be the 288gto which looked like a 308 but was more like an F40 underneath. It was a lovely shape.
If I could bring myself to own one it would be a 365 the four seater in the earlier form as I loved the cool shape. If I was going to take a risk on an older car it would be the Aston V8 Vantage, the modern coupe. These are great value and can be run slightly cheaper based on the feedback I have? I am not certain that I could stomach the reaction that Ferrari's seem to bring out in the public these days.