Personally speaking, I'd want a completely restored, daily drivable, Duesenberg J, with the optional supercharger. When those cars were available for sale, they would set you back about $20,000, which sounds like chump change as far as cars goes. but, when you consider that the company went out of business in 1937, you get a sense of just how expensive these cars are.
I remember seeing one on the Barrett-Jackson auction when I was flipping channels several years ago, that had been sitting near a pond for about 20 years or so and was made almost entirely of rust, that sold for, if I remember correctly, $1.5 million.
I'd also find someone to teach me the intricacies of repairing such a beast. I mean, I fix cars for a living, but we very rarely get anything in my shop that's got a carburetor on it, and forced induction engines don't come in very often either. I spend most of my time working on Japanese econo-boxes in various shades of boring.