I prefer to buy cars with obvious problems and get them at a bargain price. I purchased a 1995 E320 wagon for $1600 with known bad transmission, non working ac, 2 windows that didn't work, and bouncy ride. Had 170,000 miles but was near perfect body and interior (MB Tex) and had lived its entire life in the Nashville, TN area. I have repaired everything myself (replacing the evaporator was more of a project than rebuilding the transmission) and now feel that I have a car that should be very reliable for many years. The only common issues that haven't been addressed are the head gasket and wiring harness. The oil leaks are minimal and not bad enough to even cause any drips in the garage. Unless I start having wiring problems, I don't plan to replace the harness until the head gasket needs to be replaced.
I enjoy working on my own cars as a hobby and have found that with the proper information I can repair almost anything. This site has be a wonderful resource. I recently took the car on a 3000+ mile trip up North and it is a wonderful highway cruiser.
Why I like the 1995:
Last year of the E-class without Chrysler influence.
A/C system uses r134a
Auto transmission has first gear start
I6 engine (M104) is very smooth and has good power and reasonable economy (20-25 mpg).
I would be very leery of buying one of these cars if I didn't do my own work. I like to "own my cars" not have them "own me".