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A major factor is the number of parking spots you have. 10-15 years ago it wasn't uncommon to see a house in Surrey with half a dozen beat up cars parked on the driveway. Granted, outdoors under even a deciduous tree is not a well protected place for a classic or future classic.
I made a huge mistake 4 years ago when I sold my e30 M3. I compare it to this day with my FR-S. I cringe in the fact that the bmw has doubled in value. I have to admit though, I wouldn't be surprised the bmw still would be more expensive to drive the last 3-4 years compared to my now dinged, battered and mysteriously creaky Scion.
There were a lot of factors why I decided new was better. One is, your going to encounter people that know nothing about or appreciate history. Case in point, I should have kicked out my roommate immediately, when he couldn't believe I paid $15,000 for a car nearly the same age as Blake Lively.
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