Re: How far up shoud the roller be?
I think most will say that your bow eye should be below your roller, not on top as it is now. But your winch post setup looks like mine used to where you could not get the strap to the bow eye if you were to raise the roller so that it's above the bow eye. I ended up re-mounting my winch so that it was on the underside of the horizontal portion of the winch post.