If I came into scads of dosh, a car wouldn't be where I'd spend it. There are a lot of fancy cars, but I have loved the Mazda MX-5 (Miata) ever since it came out. And I loved my Audi A3. I dig just about all the Audis - the new A5, and the supercar, whatever it's called.
But I'd probably go a superclean vintage Vespa or Lambretta to go with my current ET4. And then, well, a beach house, a surfboard, the entire discography of everybody, a recording studio, and lessons for me and some mates so we could just jam econo* forever.
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*: d. boon: gone, but not forgotten.