I personally think one of the more overlooked Mercedes-Benz that is still relatively affordable is the W124 coupe. It’s starting to get in that sweet spot of becoming old enough to be classic, but all the equipment is still modern enough, both safety and amenities, that you are perfectly fine driving it everyday. Nothing will kill you in terms of maintenance or repairs, and even since it is a W124 at the end of the day, it shouldn’t be that unreliable at all. What’s not to like?