If you trailer a boat, you might run into this problem too. When launching my boat, my bow eye would get hung up on the lower roller on the bow cradle on the winch stand. Here’s a quick fix. I installed a heavy spring between the bottom part of the roller assembly and the winch stand. Now when I release tension on the bowline and the boat moves away from the winch and the cradle, the spring pulls the lower part of the cradle toward the winch stand so the bow eye clears the lower roller. Any lawn mower shop or hardware store can supply the springs needed.
Calverton, New York**_