I have an '88 300E with over 200K miles on it and its running great. Oringinal trans, no leaks... did timing chain, rails,and guides along with valve stem seals, it doesn't consume oil. If you keep up with the regular maintenance, these are great cars.
Definately suggest a set of separate snow tires for the Michigan winters. I haven't been stuck yet in three winters (knock on wood):p
'86 Alfa Romeo Spider
'84 Harley Davidson FLH"X"
'70 FJ40 Land Cruiser (basket case)