Well, 22 years ago I asked myself a similar question...what 5 cars would I want most in my garage. The list was:
MKI GT40
DeTomaso Mangusta
Ferrari 246 Dino GTS
Lamborghini Miura
an open cockpit race car (ala canam, sports racer, etc.)
Then I set out to make it happen. I have been fortunate to now have them all in my barn..sort of. (I settled for a Superformance MKI GT40, and the ship sailed on Miura prices before I could find one, so I got a nice Series I Espada that allows me to enjoy that fantastic Lambo V12 with 3 passengers. Sadly the downturn forced me to sell the race car last fall, but I had a ball with it for six years and have a big photo mural of it on my end wall.)