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If somebody else is spending money I would chose 2 most expensive vehicles in the world. Then I would sell them and buy bunch of cars from 1950s and 1960s.
Some people here dream small. My two would both be Bugatti .....The Bugatti Type 41, better known as the Royale, and the Veyron 16.4. The Type 41 would bring enough money to satisfy most any motorhead's dreams and the Veyron would look nice in my driveway.
My best friend and I made a pact in high school. Whichever of us won the lottery first would buy the other a car. Back then she wanted a vette and I wanted a viper. Now I still want a viper because they're just so sexy but I'd take a blanket send the bill to whoever was buying for a full custom restoration for my 79 as strange as that may seem.
For me, I'd have a 2008 F250 CrewCab 4x4, either a King Ranch or Harley-Davidson trim, diesel engine, automatic transmission, and all the creature comforts Ford could put in it for me. Power windows, locks, tilt, cruise, A/C, a top of the line sound system... heck, even a power sliding rear window, if they offer it.
And then I'd have a 2008 F20 Regular Cab 4x4, with a diesel and a manual transmission. No power windows, locks, or seats. The base radio. Vinyl seat and rubber floormats. No A/C and a one-piece rear window.
If somebody else is spending money I would chose 2 most expensive vehicles in the world. Then I would sell them and buy bunch of cars from 1950s and 1960s.
That one would be hard to top, and good thinking there!
But mine would be a 1965 2+2 Mustang, 289, hurst, 4 speed, 4:10 rear gears, with red velvet interior. Just like the one I had back then.
Number two vehicle would be a 2008 F-350 Scab, short bed, Lariat, in Sand color, with the 6.4 deisel.