Re: What size winches?
My Catalina 25 had a single #7 for halyards on the port aft corner of the cabin top.
That was more than adequate to get good halyard tension.
Lines were led aft using blocks at the base of the mast leading to a triple deck organizer.
boats that I sail on regularly: Pearson 28-2, Rondar 505, Yankee 30, Blanchard Junior