My five car garage would be rather large and need a ~10,000' runway adjacent to it:
I too have always loved the Ferrari 308 from Magnum P.I.:
Already have this for the family (and I like it), Volvo XC70:
For little hops around Alberta and shorter strips the Cirrus SR22-G3 Turbo (4 seater):
For those longer stretches, the Socata TBM 850:
Finally, for when you want to get around real fast the Cessna Citation X:
Optional 6th aircraft if I had an absurd amount of money. The classic 747SP, with fully upgraded avionics and engines, and a VIP interior:
Edit: Actually, for the fantasy 6th pick I'd probably go with Concorde. Can't believe I forgot her:
Droooooooooooooooooool.