The auxiliary, by the year or the hours
An engine that runs forty hours a season still needs its oil changed. Give the oil and filter a schedule of every 100 engine hours or every year, and the job is due at whichever comes first. On a sailboat that is usually the year.
The standing rigging and its age
Add the mast and standing rigging with the date it was fitted, and the yearly inspection follows. If you mean to re-rig in a given year, put that date in Service or expiry due, and Today shows it from 60 days before.
Sails, winches and the furler
Each sail, each winch and the furling gear is equipment of its own, with its own suggested plan: the sail inspection and wash, the winch service, the furling gear service. A problem you notice on a trip stays with the sail it belongs to.
Day sails and passages, and the spares aboard
A trip leaves from your home marina unless you say otherwise. For a longer passage, plan it, run your departure checklist and make a kit of what to have aboard. Spares are listed by the locker they are in, so you know what is aboard before you go.