Just as well I am not ridiculously wealthy, as my car collection would probably still bankrupt me. Still, if money was no object and I had the large storage shed and workshop to house and maintain a fleet, it would probably be a start to include the following:
1993 Mazda MX5, my current car, but modified with a supercharger, roll bar, and semi-slick tyres.
Late 80's 911 Carrera, the best expression of the original 911 concept but with 30 years of continuous improvement.
Aston Martin DB9.
VW 23 window Samba bus, white over red.
59 VW type 2 van, flat black, rat rod style. Both vans converted to 12v electrics and with the later model rear end conversion.
Late 60's Dodge Charger with big block hemi (yes I did grow up with the Dukes of Hazzard).
Gen4 Subaru Liberty (Legacy) GT wagon for a daily driver and long distance tourer.
I am sure I could fit a few others in the fantasy garage.
john