I feel the same way. I drive a classic Range Rover, and it is a lot of fun. Yes, I spend around $2000 each year getting various components repaired or replaced, but that is enough to keep ahead of entropy, and between loan payments and the higher cost of insurance I'd be spending twice that or more on a newer vehicle. Plus, I have a relatively simple machine with no fancy DRM automation crap that won't report me to the FBI for crimethink.
Apparently you're 8 times more likely to die if your car is half the weight of the one you have a high speed collision with (sorry from memory no reference, could be bogus). Add to that the over-the-top strength of the Range Rover and even though it's a classic, I think you're going to be more likely to survive in a head on collision than 95% of other vehicles on the road.
That makes sense in a simple, back-of-the-envelope F=ma sort of way. I hadn't really thought about it from a safety perspective, though; it just suits my needs well. In general I'm happier to economize by buying really nice stuff that's cheaper because it's used, than by buying something newer that's just cheaper. It becomes an aesthetic thing - a feeling of shabby luxury suits me.
