Sounds like a reasonable plan and I like the idea of getting to know your boat. I try to do each maintenance item at least once. I do all my own winterization and commissioning. That gets you close and personal.
On the other hand, I have many things still on my improvement list from several years ago. I don't get to them, because of the all too common unplanned expenditures. For example, I now need a new $3,000 turbo. Ugh. That will delay the list again.
Perfect example of why I think this project is going to take about three years. Water maker roller furlings genset and new sails will cost me more than 20 grand alone.
Oh well cost of living my dream as far as I see it.