Winterizing is easy. I don't. *grin* Once the water temp gets close to freezing I keep a small oil-filled radiator on the boat when I am away and a diesel heater to stay cozy when I'm aboard.
Provisioning is very personal as so much depends on taste and cooking style.
I have a dry & canned goods stowage list on the boat for where things are. I keep a print-out in the galley. When I move something from deep stowage to the galley it gets crossed off as "used" even though it is still in the pantry. The list drives a shopping list.
For fridge, freezer, and pantry I have a whole series of menu plans and shopping lists from deliveries. The menu plans drive shopping lists that get checked against the pantry before I go shopping.
I'm not very good at repetitive tasks so I've set this up to take as little attention as possible. Every year or so I empty all the deep storage and repack it, updating the storage list at the same time. When I defrost the fridge and freezer I make sure older stuff is used or pitched. I inventory the pantry while the fridge & freezer melt. Then everything gets scrubbed.
Most maintenance on my boat is done by association. If I'm changing the oil in the main I do the gen and outboard at the same time. Same with fuel filters. I rebuild winches when I can't quite remember when I last did them. Whatever is close by or uses the same tools and supplies gets done. I've started maintenance check-lists a bunch of times but for my personality they simply haven't been sustainable.