I'd start with my great grandfathers '31 coupe, my Grandfathers 1st tractor and plow, my fathers '66 Super Sport, my mothers '69 Camaro, and my '87 Mustang. Throw a cot and a fridge in the corner and pay a car nut to live with them until they are better than original and thank ****ing god they are finally out of the working shop so I can get something done. I guess start a '32 rat rod project in a slot and keep rotating through the newest/baddest lambo style of import in another. I could see an ultra small helicopter being handy and keeping a decent boat in another. Hopefully there is a good enough area left to put in a couple well polished brass poles with a pair of monster big screens and recliner seating for the good times with a few friends.
The daily drivers can sit in the rain.