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A brand new Velar for cruising around and Jag F type SVR coupe for fun ;)
 

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It would not be a Land Rover Defender. Since the reason Defenders are worth 100k has nothing to do with the Vehicle itself.

You said blank check right?

It would be a MARUSSIA

https://en.wikipedia.org/wiki/Marussia_Motors#/media/File:Marussia_B2.jpg

And secondly a Bugatti, Zonda, upper level Ferrari or Lamborigini collectable. Those cars are annual passes, as you get older - to keep pulling young dumb tail - because car leaves no doubt about the drivers financial picture.

A hot 22 year old will stare at an older man in a Bugatti. She won't stare at an older man with a Land Rover.
 

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A brand new Velar for cruising around and Jag F type SVR coupe for fun ;)
VELAR ????

That's freakin lame dude. That's not even a real Land Rover. It's a TATA.
 

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Drives like an old man
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Probably a GMC Yukon Denali. While exotic Italian cars are nice to look at, history shows the most common view to be of the undercarriage on a lift. No thanks. The Yuke gets you anywhere you and 7 other people want to go very comfortably, has American reliability (very high) and is good for all occasions. Plus, you can get it fixed literally in any town in the US. Don't give a crap about young, dumb tail. Got a wife.
 

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Bleeds Green
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The 1963 Ferrari GTO - $70 million. I'd drive it around the block once, listen to the engine sing, and then sell it to live a very comfortable life.
 
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The Car i could resell for the most amount of money possible. Then i would buy (See below?)

2020 Chevy Silverado 3500 Duramax and a C8 Corvette and a 2021 Suburban High Country with a Duramax, a 2020 Chevy Camaro ZL1 1LE, a 2006 Chevy Silverado 2500HD Duramax and a 2020 GMC Sierra 2500 AT4 with Duramax.
 

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The Bugatti type 37 Atlantic, worth over 100 milion, and then sell it and buy a mansion, and a Bowler Bulldog.
 

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Range Rover Mk1 (1970)
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If I could buy any car, it would definitely be a Ferrari Pininfarina Sergio, this is the car of my dreams.
 
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