Thanks for posting the pictures. They are helpful. As others have suggested, I would find a way to raise the roller some. When installing your new u-bolt, you should consider running those outside nuts all the way down to the shank. This will help reduce the leverage on the u-bolt. All of my boats have been configured like that.
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.... so, yeah, you're gonna have to make the adjustments at the winch stand.
(I've seen some people take nearly 20mins trying to get their boat trailered just so, moving the vehicle - moving the boat - re-moving the vehicle - rinse/repeat 
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