The short answer is that I don't think you will gain any advantage. The time it takes to dress the chain is probably about the same as what it will take to remove the guard and replace the chain. Using the correct sharpening file makes the sharpening process quick and efficient. You only need a couple of strokes with the file to restore a sharp edge.  Err on the side of sharpening the chain more often than less. You will save time sharpening the chain frequently. I sharpen my chain every other time I fill the gas tank.  The best indicator of the condition of the chain is the shape and size of the chips removed when cutting. Nice large and well-defined chips indicate a good sharp chain.