I aim to minimize both pixels and surprise. I typically prefer ' in order to minimize pixels, but " instead if the string has an apostrophe, again to minimize pixels. For a docstring, however, I prefer """ over ''' because the latter is non-standard, uncommon, and therefore surprising. If now I have a bunch of strings where I used " per the above logic, but also one that can get away with a ', I may still use " in it to preserve consistency, only to minimize surprise.
Perhaps it helps to think of the pixel minimization philosophy in the following way. Would you rather that English characters looked like A B C or AA BB CC? The latter choice wastes 50% of the non-empty pixels.