Updated Winch Roller Setup
 

Well from comments made I tried to find a solution with my sister in law @ trailer company. Basically my winch plate didn't allow for the strap to go under the roller without rubbing on it quite a bit.

So had this recommended as an option which installed quite well, was inexpensive and achieved the end goal.

much better and now safe

Isn't the winch on backwards?

&$)(#&($&

Now it makes sense as to why it seemed odd that the strap was going through the dang bars that hold the gears. Also the handle would be more convenient on the other side.

Overlooking the obvious. Will be reversing it tonight. Thank you.

Also got me 2 seats with pedestals for $50 today!

lol i just figured you had something in the way on the other side for the wench handle like a jack handle.