difficult question this. 20 years ago I would have been debating between a 458 Italia ( or whatever preceeded it) and a Lotus Elan probably choosing the Elan on the basis that its always more fun to thrash a slow car than to be holding back in a car thats simply too fast. But nowadays I've come to the conclusion that you cant have any fun in a fast car . Just too much traffic and too many speed limits. Or maybe I'm just too old.
So my ideal car would be one the chauffeur was happy with. As a young man in a steel industry that still did things the old way, we had the use of 6 chauffeur driven cars. Old RR at one firm until they became too unreliable. But I've never forgotten the sheer luxury of sitting in the back seat reading the paper whilst someone else coped with the traffic.. So it would probably be a big Merc since RR and Bentley are a bit too flash ( sorry Boshly) for my taste.
Then there would be my wife's car, a Smart roadster that will probably be with her when she meets her maker. And a couple of decent motorbikes. And a Radical for trackday and a bit of club racing.