I don't think I understand what you are asking. The entire windlass will mount in what ever plane it is installed in. If it is parallel pulling up the chain, it will be parallel deploying the chain. I don't understand how it would change orientations, or how one side of the gypsy could be on a different plane than the opposite side?@colemj - since your stating that the vertical gypsy needs to be in plane with the chain - this is what I am trying to confirm, however, is there a concern about the windlass being sloped during deploying of the chain? Obviously the side where the chain leads to the bow isn't a problem, but is there a problem with the side coming through the hawse pipe?
I've seen a few boats solve the problem by adding a roller in front of their windlass to draw the chain down and parallel to gypsy, however, I am not a fan of that design as it mean there will be additional effort on the windlass to retrieve. Since this is a new install I can get around this by angling the windlass to match the chains angle.