The angle is a little harsh at the bow eye. did you consider a safety chain from the top rung of the ladder? I'd rather secure that way after winching on than having lot of pressure pulling down on the eye.
btw, the pipes over the transom? why?

"the pipes over the transom? why"? becuase they were there when i bought it. i plan on installing new exhaust when i put in my 1000hp blower motors. but the drives are so high that fitting 5" tail thru the transum may be tuff so the new pipes so they may go over transum as well. i guess i could remove the internal tie bar when i try to fit the new exhaust. i plan on installing an electric winch in a few weeks that will sit a few inches higher and be a stright pull against the bow eye.

I just noticed how high the motors (air filters) are, looks like thru transom would have been tough angle.

does the trailer have electric brakes?