the routing you propose would indeed be shorter and have a bit less friction. But I could not come up with an elegant way to get the lines from the corner of the cabin trunk to the winches on the coaming. Especially with the dodger in the way, but regardless: the lines have to either come straight aft to the winches and become a tripping line for every egress from the cockpit, or somehow get around the corner of the cabin to the deck. Never could figure out how to do it. So I ran them forward, down the side deck, up through a conduit in the coaming and turned them through a custom over-the-top fitting. In conjunction with the fact that the 25 foot boom can be eased 150 degrees or so, the single line is 280' long!

Ferrules along the boom, CNC machined from G10 with 316 SS insert bushing, carbon fiber taped to boom:

Lines come back along the cabin-deck crease though ferrules machined from 316 SS to match the angles. These are fastened into tapped G10 inserts bonded into the laminate so they cannot leak. Also visible is one of the deck prisms, annealed glass with a machined G10 frame bonded into the deck, again to try to eliminate fasteners and leaks:

And then to get up to the winch in a tidy way, a Harken foot block leads into a conduit through the coaming to a fabricated over-the-top type block into the winch. Inside is a Harken sheave. They were boxed out this way so I could put a clam cleat on top to make hand sheeting easier, that project is waiting for me to machine a SS clam cleat so it can be welded in place: