Fun Hypothetical ...

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1 '03 Ford Model A
1 '34 Ford three window coupe
1 '49 Buick Roadmaster
1 '58 Vette fuelie
1 '62 Porsche 356B Notchback
1 '63 Vette split window
1 '64 Ford Mustang
1 '66 Pontiac GTO
1 '74 Porsche 911 RSR
1 '87 Buick GNX
1 '92 Porsche 959 Komfort

That would make a nice start
 
How about:

1 Ferrari Dino 156-Love the GP cars of this era
1 Ferrari Dino 158-Ditto
1 Ferrari 275 GTB/4-Gorgeous
1 Ferrari 250 LM-Always loved the look of this old racer
1 Ferrari 330 P3-Ditto
1 Ferrari 365 GTB/4-The Daytona, fast and pretty
1 Maserati Ghibli Spyder-Rare and gorgeous
1 Lancia Flaminia 2.8 Convertible-Almost bought one in 1980
1 Lancia Fulvia Coupe-love this little car's lines
1 Lancia Stratos-mean little rally car
1 Full-time Italian mechanic with machinist, casting and sheet metal skills-would be needed to keep all of the above running.
All of the above would be street driven regularly, except for the two 1.5 liter F1 cars. They'd be for track days and maybe vintage racing events.
Am I already overdrawn on my winnings?
 
I'd stay with what I have, having a nice car on today's roads is a pain in the neck.
But I might get a race car
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Since I would no longer have a "job", I would probably buy vehicles like I've had in the past. You know, the ones you were sorry you sold. In my case, a Chevy Corvair, IHC Scout, Plymouth Scamp (the pick-up truck), maybe a Plymouth Duster (slant six). Do as much of the restore work as I could do myself, and have the work I couldn't do done by others. Then, I'd probably add some miscellaneous cars that interest me to the collection; a Model T, a Stanley Steamer, a Studebaker Avanti, a Buick Reatta, perhaps a "rat rod".

Bit of a "mixed bag", eh?
 
For the price of one specimen of some of the cars named above, you could get a whole herd of cars! My first 3- I think one each of a nice new Mustang, Challenger, & Camaro would make a great start. Think of all the fun comparison testing you could do!
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A ford excursion with a cummins diesel, a built nv5600 tranny, 4 wheel drive, and a kore suspension.

And a porsche 911.
 
That's a tough one. I like so many -- although my list is somewhat simple (less exotic).

- Raptor Crew Cab or Ram R/T std cab
- SRT8 Grand Cherokee
- Boss 302 Mustang
- Durango Citadel or MKT Ecoboost
- Challenger 392 Green with Envy
 
AFTER purchasing the residences, taking care of my kids' futures, and investments;

A FULLY prepped (by Malcolm Wilson Motorsports, and others) Escort Cosworth RS, or WRC. Capable of 800 (unrestricted) AWHP, with a strong sequential 6 speed, and weighing
A Noble (or whatever the company is now called since the buyout) with a FULLY built, boosted, Coyote, OR a built LSx type engine, starting with a C5/6R block, and of course, a strong custom built sequential gearbox/transaxle.

A Mosler MT900R/GT3 with at least a 1200 RWHP LSx type powerplant sitting in the middle, and a STRONG custom built racing sequential gearbox/transaxle.

Either a modded ZR1, or a modded C6RS, AND a Boss 302 Laguna version (SANS the ugly paint accents
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) as daily drivers.

Above is a good "start".
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