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The one issue that's unique to the 380SL is the timing chain; it's not that the single-row is the Kiss of Death, but it does need more regular inspection and service.
The AC system you're looking for is the one with the horizontal row of pushbuttons. The earlier system, with vertically oriented buttons, is even quirkier and more taxing to keep going, though neither will win a HVAC Design of the Decade award.
All the above points about buying a 107 apply to the 380SL, as to all models of the 107.
The 380 is the least powerful of the 107 models, but I note owners tend to find it quite adequate for most driving, and it's also the least thirsty; should be able to average 18-19mpg or so as I recall.
The second most important aspect of a low-mileage car is how well it's been stored, as reflected in the results of a detailed inspection for rust and the state of the interior and paint. The MOST important aspect is how well the POs have kept up with all the bits that deteriorate: suspension bushings, window/door/top seals, brake lines, belts, etc. etc., and how well POs have kept all the systems including AC and cruise control operating. If your priority is trouble-free motoring, a well-maintained example at 200,000 miles can sometimes be a better bet than a cosmetically pristine example at 50,000 that's been stored to mechanical death.
Having said all that--Drive the car and check ALL the stuff that's supposed to work, down to things like the glovebox light, seat adjustments, door lock system, wiper blades, and radio antenna. You're looking for evidence of an owner who's obsessive about keeping everything going even if he doesn't drive it much. If it passes that level, then get an MB pro shop to go over it and tell you everything it needs with price tags and urgency ratings. Then add $2K in your thinking to cover whatever got missed. If at that point you're ready to do it--welcome to the club!
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Craig Bethune
'97 SL500, 40th anniversary edition
'04 Olds Bravada (SWMBO's)
'06 Lexus ES330
'89 560SL (sold)
SL--Anything else is just a Mercedes.
(Kudos to whoever said it first)
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