I've thought a lot about this in the past.
The first step is to aside enough so that no matter what happens, I don't ever ever have to work again. Then help out family members and friends. Then start working on building our dream home.
Back to the vehicle acquisitions. In no particular order:
Early 70's Volvo P1800ES wagon
Late 90's Ducati 916 SPS
Singer Porsche 911
I'd probably turn my current 1LE into a ridiculous track / street hybrid (gutted, full cage, built LS7, etc)
All season daily driver: VW Golf R
Some random pickup truck used for everything else would round out the stable
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