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Every year:
drain raw water strainer, muffler, water heater, and fresh water system
Oil and filter. Trans oil every 2 seasons
Disconnect hose to raw water cooling pump and drain. blow through the hose to ensure it’s clear. In spring you will insepct the impeller
While pumping out holding tank before haul out, use pressure water system to fill toilet bowl with fresh water- leave hand pump valve open so that vaccum can suck the water from the bowl, rinsing the hose and ultimately leaving it the pump assembly and the bowl empty.. No need for antifreeze if this is empty. I leave the deck fitting open over the winter.
Pump antifreeze through shower pan, fridge drain, water tank through pressure system via head and galley, plus galley foot pump
Replace the joker valve in head, lubricate the heck out of every thing else. If you don't do the joker valve, you will find black water back filling into the head in certain conditions.
clean filter screens in shower pan pump (under foreward end of port settee, and below galley sink
Spring
blast furler head swivel bearings clean and lubricate. This can cause enough friction under load to cause a halyard wrap. Dangerous.
Lubricate whisker pole
Inspect belts
When mast is down,
clean, grease and inspect the masthead sheaves and axles and bushings.. This is so easy it makes no sense not to do it, and you can inspect the halyards at the same time.
Since you are at the mast.... see below - really good advice from Chuck S in Maryland. Simple stuff that together makes for a big improvement in reliability and enjoyment.
Earlier I reported that I raise the mainsail on my 36 ft saiboat by hand. Well I couldn't do that when I first got my boat and needed to use a winch on halyards. My sailing friends told me that was normal and winches were always necessary to hoist such large sails. My mainsail weighs only 55 to 60 pounds, so I thought they might be wrong. Later, I spent some time checking all of the mast base halyard blocks and freeing a few frozen sheaves in the deck organizer, I found I could raise the mainsail by hand very easily. These sheaves are deceptive when frozen and allow a halyard to pass unimpeded initially when there is no load, but once the strain comes on, if they are frozen, the halyard becomes bar taught and the job requires a winch. I also learned from reading the winch catalog that the largest loads; the genoa and main halyards work best if reeved along the most direct path to the right side of a winch drum. So now I pick the clutch directly in line with the right side of the Starboard winch drum for my main halyard. All my winch drums turn clockwise. My genoa halyard is reeved through the clutch directly in line with the right side of the Port winch drum. I run the spinnaker halyards through the outermost clutches and all the other lines have lower loads so can be run as you like. And I label the clutches.