Are the boat skids as low as they will go ?? If not you may be able to drop them down and make up for the gap. Otherwise it looks like you may need to drill another hole for your winch head, and raise the bow roller up ... or else get a new winch stand.

What I'm talking about, when I say drill another hole for your winch head, is :

looking at this picture ... the bolt is in the lower hole of the winch head & that whole section needs to be raised up so that the bow roller fits snuggly against the bow of the boat in front of the bow eye ... so that the front end of the boat doesn't move up/down once it's winched up tight and ready to tow.



Your roller assembly obviously is not adjustable, but it does look like the main frame head is "capped" onto the bottom frame and held in place with that bolt (which I assume goes all the way thru to the other side). Whether or not there are already other holes under that cap, you won't know until you unbolt it and lift it up. If there are other holes, but they don't line up with the same distance needed to push the bow roller up against the bow of the boat ... you'll just need to mark it and drill thru both cap and bottom frame.

And NO, I'm not a mechanic, and am merely suggesting an option ... based on what I can see/determine from your pictures.