You would have to turn the winch around so the ratchet worked in the right direction. Worth a try if it's easy to do.
That way you will know it the angle is causing your problem.
Use google images "boat trailer winch stand assembly" and for every good setup you will see 100 bad ones.
I put it down to lazy or dumb trailer manufacturers.
Doesn't look like I will be able to turn it around. Do they make winches that are made to pull from the top?