I am slowly restoring a 1963 220S and having a great time. I love the problem solving. Here's my currant quandary. On long hills (going up) I do fine if I have a lot of momentum (55 mph) but there is this one hill I have to navigate daily that causes problems. I hit the first gradient rise at 40 mpg, continue to accelerate to 45 when the gradient increases again. (This is a very steep hill, 3/4 mile long with a truck run-away ramp.) The car has an automatic transmission and it is in third gear at this point. Slowly and gradually I lose speed until the summit when I am down to 20 mph. The gearing doesn't shift down to second gear until about 17 mph. The kick down switch under the gas pedal does not work. I can manually shift into a lower gear but I hate to do this (gotta baby the old automatic.)

What could be to blame for this?

The car has 87k miles and was a barn find that was traded a couple of times before any real miles were put on it by me.

Thanks for your ideas,
David

You are actually intended to manually shift the automatics to a lower gear in these cars. I prefer that to using the kickdown switch simply for the joy of doing so and only use the kickdown if there is a much more immediate need such as closely following traffic. You are doing nothing wrong by dropping it down a gear and will soon realize how much you enjoy doing so. Remember, these cars are build to be revved high, that's just how they were designed, they love to rev. Also, when starting off from a dead stop on an incline the same downshift is expected, you will see your car in a whole new light!
When I first got mine I thought it was a dog, worse than aW123 diesel, but once I realized how they were intended to be driven I now enjoy the relative sportiness of it. Don't get too "Fangio" in the twisties tho, these are still grand tourers, not sports cars, and you do have a swing axle under there that will remind you of it's presence if pushed beyond it's limits.

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1962 220SE W111 Coupe, 2nd owner

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The Coupe Group (W111/112 coupes and cabs) official website
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You'll suddenly learn a new dance with the steering wheel, the Juan Manuel Fandango.

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Looking for Early 108 windshield surround wood in decent-to-good condition.