[Aerkuld]

If ever possible I think it would go like this...

I love the idea of a 997 GT2 for when the others are in the garage or it's raining.
Ferrari 250LM
A classic 4 1/2 Liter "Blower" Bentley

I suspect that the last two wouldn't be that available so I'd settle for these as replacemants;
In place of the 250LM I'd make do with a Ferrari F40 or if forced to go new I suppose a 430 Scuderia would do.
For a cool cruiser maybe a Bentley Arnage T in place of the 1920's Bentley.