I think you want the winch ABOVE the bow eye . . . otherwise, during the last few feet, it will be trying to pull the boat DOWN instead of lifting it up, so that would make it harder to pull boat up on trailer. That roller isn't doing anything except getting in the way of the winch cable! I'd just cut off the bracket right aft of the winch and eliminate the roller so it doesn't interfere with the cable. Of course if you just dunk the whole trailer and float the boat up to the winch, it probably doesn't matter!
Understand that these comments are from a guy that's used a roller trailer and Powerwinch so trailer NEVER gets dunked, which is why the 30 year old trailer still has it's original springs and axle! Picture below shows my winch setup; bow eye is located between the 2 rollers. I added the Rustoleum painted extensions to roller bracket to make room for the pulley that's attached to hook. (Winch cable runs thru pulley and back to winch stand to double the pulling power of the winch.) I need the roller stop to keep boat from coming too far up on trailer, which would allow aft rollers to go past transom! This setup has worked well for about 30 years with very little maintenance required.
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