Jason: your dovetail isn't too bad, especially for your first. Take the advice given above, and grind the safe side of the triangular file until the edges are sharp, with no roundness at all. Your dovetail is almost perfect on the left side of the barrel, and has dips in the corners on the right side. Filing FLAT is something that requires concentrated attention. I use a felt pen to make the angled flats on both sides black, and mark the depth of the rectangular cut with a Vernier's calipers; on a rear sight like yours, .030". Then when I'm sawing and filing out the metal, I am careful not to lose that scribed line. Breaking the edges of the sights male dovetail, and or using a graver to cut a sharp inside corner, is necessary before you try to drive your sight into the dovetail.
Keep practicing...you'll do fine.