As an anecdotal data point, when I hit "edit" in my phone favorites list on the iPhone, I always saw the "drag handle" as a little list, which I understood as a clumsy stand-in for "reorder this list." The "drag handle", as a representation of a little surface designed for friction so you can put a finger on it and drag it, never occurred to me as a possibility, though I understood it in other contexts. Apparently users can creatively make sense whatever they see even if the intended analogy falls flat.
I think the popularity of retina displays will result in a clarifying divergence of these homographs into different representations. A few years from now we will see the collision of these different meanings as an artifact of low-resolution graphics intended for low-resolution displays. But a few years beyond that, I think we will tire of subtle distinctions and decide that homographs are not any more difficult to deal with than subtle visual distinctions. This collision has not resulted in significant user confusion; in fact, it has taken an unusually observant person to point it out to the rest of us, who were happily using these interfaces without difficulty.
I think the popularity of retina displays will result in a clarifying divergence of these homographs into different representations. A few years from now we will see the collision of these different meanings as an artifact of low-resolution graphics intended for low-resolution displays. But a few years beyond that, I think we will tire of subtle distinctions and decide that homographs are not any more difficult to deal with than subtle visual distinctions. This collision has not resulted in significant user confusion; in fact, it has taken an unusually observant person to point it out to the rest of us, who were happily using these interfaces without difficulty.