I have a neighbor across the street who has to get rid of a W201 1988 190e with 87,000 miles on the odometer. I really don't know too much about them, I have had a few of the older cars (w119, w115, w126), but none of the real "modern" cars. He needs to get rid of it due to his landlord getting sick of looking at it. It is sitting on 2 flat tires (front) has a broken front windshield, drivers side rear quarter window and has a cracked front bumper cover. The body is mostly rust free, and paint is not that bad. I think that is the bad stuff. I have spoken to the landlord who will get me the title. I figure I will give the owner a hundred or so dollars. I have no idea if it will even start.
So what should I look for besides the obvious motor starting. I don't think I will be able to test the transmission. I want to use it on weekends, as I have a Miata that I commute in and will use it in the winter. Are there any "trouble" issues that would make a project unreasonable. I figure the transmission is going to be the main thing.

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Currently
1991 Mazda Miata 174000
1991 Subaru 189,000 Winter beater

got rid of:
1984 VW Vanagon 195,000
1976 350SE Euro 185,000 KM
1973 280SE 4.5 (boy do I regret that)
1980 280SE European W126 4 speed manual (miss it)
1989 BMW 735iL 119000 (good riddance)