I hope you are closing the through hull valves when you leave the boat. This means I cycle the valves, except the overboard discharge, every time I use the boat.
I change the oil in the engine and transmission when I winterize the boat. I change the fuel and water filters during Spring commissioning.
You might check the coolant level and transmission oil level, also, if you are checking the engine oil.
Be sure you check the float switch operation of your bilge pump. My wires were pinched and eaten away so the float switch didn't run the bilge pump.
"Inspect all wiring" is rather vague and ambitious. You should have a specific planned inspection for what is accessible.
Your sails need occasional cleaning to remove salt and dirt to give you better performance.
Inspection may not reveal problems, so a planned replacement budget may be a good way to address failures that are sure to rear their head, such as water pump impeller, battery, standing rigging, head rebuild, water fixtures, electrical devices (gauges, fans, light bases, outlets, switches and breakers), etc.
I have seen the use of checklists that would cover much of what you are trying to accomplish. A checklist each for opening the boat, leaving the boat, Spring commissioning, winterization, race day, or a long trip. This would entail much of the inspection in your schedule as you go through the checklist and operate the items.
-just an opinion