dclukin, im not so sure being "smart" has as much of a correlation to being wealthy as it used to. There are 90 billion ways of making lots of money in todays corporate world... being in California, in a state where MB's are about as common as a mailbox, i stopped making assumptions about the people who drive new Mercs long ago.... sure there are the "educated" guys and gals who have the harvard degree and have a stable full of new Mercs, but for every one of these, I cannot even fathom how many people there are in CA who drive brand spankin new Mercs and have a standard or sub-standard education that have found wealth in business, arts, and other forms of "work" that bring in large amounts of monetary profit. But in the end, its all the same, and the stigma of driving a new benz still applies for those who wish to put people on a pedestal for their choice of automobile...
my thought on the topic of this thread is, that as someone mentioned earlier, it seems its not the year/model that people pay as much attention to, but rather condition.... which I have realised can fool a lot of people. Back when I had my first W123 people thought that thing was BRAND NEW.... just because it was in showroom cosmetic shape.... and probably combined with the fact that old benzes when well cared for, age nicely.. like wine.
Besides, only the shiny new and "new" looking old Mercs are the only ones that get any sort of attention with sooo many of them on the roads here.
Id like to think that driving an MB doesnt represent monetary wealth, but perhaps the preferance to drive a car that represents a company that has, or had, a passionate drive to build cars of unimaginable engineering and design quality, and in a way, paying homage to a company that has built cars for over 100 years, of unprecedented technological prowress, that has set a benchmark for longevity with their older models.... but then again, all too many people see the 3 pointed star and just see $$$, and nothing else.
I hafta say, my mom bought a 1989 Honda Accord SEi back in 1990 to use as a commuter car for work. That thing racked up 215K miles before the dummy at the shop didnt tighten everything up after an oil change, which in turn left my mom suddenly stranded on the side of the freeway with a burnt up engine.... we were thankfully given plenty of $$ for that mistake and ended up better off than to begin with on that deal. But that car sure was a great car, and it looked just as good in 1998 as it did new, out here in CA without the rust problems....
to summarize the more relative parts of this post, generally spekaing people see a clean well cared for benz of any vintage and think wow. Newness and model doesnt seem to matter.
Happy Motoring!