If your winch is anything like the original winch on my H23 trailer, it really just needs to be replaced. However, this is NOT a boat that you can drag up to the post - I'm sure you realize that. You've got to float it up - and even then it ends up not being all the way up to the post once you pull it out!!!
Becuase of the trailer tilt, the boat will always end up behind the winch post by a little bit (see picture). My current solution is to winch it up on dry land with a cme-along around the keel, but what I am going to do is install the winch farther back, with a 2-position bow stop, one for loading it, one for trailering.