I swiftly proceeded to buy myself a cheap Plane, the fancy cars can wait for later, and I already have a nice apartment.
The only problem I now find, is that you need to call a number on the phone to have the plane delivered to the nearest airfield, which would be fine - but it eliminates the point of owning a plane, since other "free" planes are going to be at the airfield anyway.
I can see why they did things the way they did, but why buy a plane (and pay to have it delivered) when I can grab a freebie at the same location?
Either way, I'm having fun with me and my friend setting challenges to land the plane is obscure locations on the map for self shot opportunities.