First I'd get a nice little place of my own, with a garage like Jay Lenos' (Climate controlled, of course!)
Then a 300SL Gullwing AND Roadster (So I wouldn't have to choose).
A late 60s SE Cabrio with the factory 5 speed stickshift would be nice and, for my everyday 'beater', maybe a late 60s SE sedan, also with a stickshift then, one of those 230S Finnie Wagons (The perfect thing for flea markets!) I would probably add some others but I'd need some time to think about it.
And finally, after satisfying all my 'instant gratification', I'd restore the car I had in High School, my 1961 180b Ponton. It's the one rusting under a tarp in my driveway - the one I keep saying I'm going to restore when I win the Lottery!

Happy Motoring, Mark

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DrDKW