Answer: For the purposes of answering this question I’m going to have to make the assumption that both cars are in fine comparable mechanical condition.
The first car would be considered a “survivor” and the second car would be considered “restored.” Comparing a survivor with a restored car is interesting because the distinction between an asset and a liability becomes very blurred, and sometimes even reversed.
Let’s look at the “survivor” first. The paint is a bit dull and it has a few chips. Dull paint with chips would normally be a liability. But the fact that this car has survived more than four decades with these few battle scars makes it a tremendous asset. The air-conditioning and the original documents are also assets. Original survivor cars are like real estate in that “they ain’t makin no more,” so it would be very difficult to find another car like this. There are collectors who buy 280SLs, and there are collectors who buy “survivors” so when the time comes for you to sell the car, this “dual market” gives it great intrinsic value.
Now let’s look at the “restored” car. It’s fully restored and it has a great paint job, which are big assets. The rust issues have been tended to, which is an asset, but it had rust, which is a liability. As with the first car, the air-conditioning is an asset as well. This car will likely appear “as new” or possibly even better, however, when it comes time for you to sell this car, you will be competing with many sellers of similar restored cars.
There are two schools of thought that come into play here, and which school you subscribe to will determine which car you buy. If you value originality, along with the patina that comes with age, buy the first car. If you like shiny new things, buy the second car. If you’re still undecided, look around your house. Is it filled with antiques, or is everything new and perfect. You’ll know which car to buy.