It looks like the rudderpost is at the leading edge of the rudder - probably a SS bar. There may be a fiberglass wrapping that you could grind down, but going beyond that to cutting the post would probably not be a smart move. You may have some "wiggle room" from removing the cutlass bearing, but the drawing on Sailboatdata makes it look like the shaft has a lot of solid keel/sternpost fiberglass holding it very straight.I thought about that I wonder how much meat is there and how much I would have to cut I guess if it wasn’t much I could glass it back when I got it in