Actually By-Tor, I suspect many of us actually do buy a 'rep' car ... sort of. More properly, I suppose 'used gen' might be the better term.
Look at Dave123, he bought a 2008 SL55 which can be had (here in the US anyway) for less than $70k if one shops around. Less than half the cost of a new one. Smart money, well spent, I say ...
I almost never buy new anymore. I would much rather spend $30-$40k on a quality used car, than eat the depreciation of a new car. You can buy current body style SL's for that price (even older AMGs), as well as many of the other 'exotics' in this thread. Sure there are more expensive rides here that can't be bought for that, but they can still be had at a deep discount over the new price. Very few people (are there CIS's?) are going to know you didn't pay full price when they see you driving by. I'm looking to replace my 'bought off the Bay' XK8 right now, and can't believe the prices I am finding for quality low-mileage cars.
In short, I believe rep buyers in general are pretty savvy with money. As Dave123 also said, look what you can do with the money you save buying reps ... or even cars ...