Originally Posted by 230/8

Personal preference would be for an early small-bumper model simply because they look better, cleaner, and have simpler easy (in my opinion) to maintain systems. The cast iron engines are old-school engineered and virtually bullet-proof. If not one of these then seek out a late 560SL, an 1989 if possible.

Most folks who are far more experienced than me when it comes to buying used cars will always recommend buying a car in the best possible condition that you can find. Setting a low-dollar budget limit on a Mercedes is, to my mind, a virtual guarantee you will need to compromise on condition which always translates into you spending money to remedy deferred maintenance items. This is seldom (never in my experience) cheap to do on a Mercedes unless you possess good DIY mechanical skills and, hopefully, some experience with the German way of designing and building vehicles of earlier vintage.

Just my two cents; best of luck in your search. Mercedes roadsters are under appreciated, and, fortunately, somewhat under-valued in the market.