I think the biggest risk would be parking lot dings, rock chips, fender benders, and such. I go to great lengths to protect all of my vehicles from those hazards, but they still happen. Like Karl suggests, it is impossible to predict the behavior of stupid people...and there are a LOT of them out there. It might depend on where you live (traffic, congestion, attitudes, roads, mentality). Also how often you are willing to pay to have those blemishes removed.
As far as actually driving it though, isn't that what it's made for? However one factor I might add to your list of criteria (weather, etc) is having the flexibility to be late getting somewhere in the occasional event the car lets you down.
Parking lot commandos is my biggest concern.
About a week ago one got my wife's car on the left rear fender.
Over the years I have had several dings caused by those thoughtless imbeciles.
A couple of them I caught in the act and the rest managed to slink away with out owning up to their mistake.
I have had a car that was parked out by it's self at the end of an empty parking lot get hit.
The chance of a traffic mishaps is something that helps me keep my blood pressure up.
I live in a tourist town and I am convinced that the people coming here on vacation brains have taken a vacation in a different part of the country so I am constantly on the look out for some nit wit.
Had to lock the brakes to the point of squalling tires twice yesterday for cars pulling out in front of me while I was out running errands.
Got home and swore never to go out again but later that evening talked myself into taking my sweetheart for pie and ice cream at a little restaurant about 15 miles out of town.
A nice little stretch of turns (some tight) on the way and lucked out with no other cars in sight.
On the way back was the same and this is where driving vintage tin can be a problem.
I was laying into a fairly hard right turn when I hears a pop!
Didn't feel anything and the car kept going smooth and handled the rest of the turns fine but I am going to have to make time to go over the car looking for ant visible cracks or what ever.
Five or six years ago I was pushing my X pretty hard and luckily it waited until I got in my driveway for the left radius rod to break letting the tire move back against the fender well.
There have been many times when I wished I was driving a big heavy beater that wasn't in my name so I could ram the hell out another car and walk away.
There is a W.C. Fields movie called Road hog where he buys a fleet of cars and crashes into other cars he deems to be offensive.
I understand your feelings Dr Jeff but we must curb those thoughts and remember our Hippocratic oath lest we become no better than those that irritate us.
However rather than crashing into the other car and then having to walk home I think a couple of silkworm missiles mounted on each fender and puncture proof tires for driving over the debris would be more efficient.
I have read a couple of SiFi's where highway duels are the norm in the future kind of like old wast gunfights.
Here is a clip from The field movie.