I might be biased since I have a 84 but I think the later 380sl (84-85) are the second most desirable cars in the 107 series. The timing chain issue was solved and the a\c system was changed to a more reliable system. I find that they have more than enough horsepower for tooling around town in and the gas mileage (18 city/22 highway) is pretty decent for an almost 2 ton car with a v-8. They are marginally slower than the earlier 450's and probably faster than the later 450's which were stuck with 3 speed autos and cobbled on anti-pollution equipment. Both the 450's and 560's are gas hogs.
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As for the timing chain issue I personally think its been blown out of proportion. Change it every 40 -50,000 miles and you should be okay. With the amount of driving I do on my car that works out to be about once every 15 years.
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Unless you have a need for speed buy a really nice 380sl and get used to a goofy grin everytime you'll get from driving on a sunny day and thinking about the money you saved