Boat/trailer winch

I can't quite see from the photos, but it looks like the rear of the boat is overhanging the bunk it rests on. That's not a good idea, as it travels down the road it will eventually dent the hull right in front of the transom. The entire rear of the boat should be on the bunk. Your boat looks almost exactly like mine, and I wouldn't worry about tongue weight increasing. I had to move my boat forward for the same reason and it amounted to nothing for handling or tongue weight.