I think from previous posts you use omnifocus (correct me if I am wrong). Do you set the repeating defer date to the 1st and a due date lets say the 3rd or 5th? Or flag it? or...?
Short answer: Yes. Well, sort of. I put it in the calendar as a daily repeater, or an every-two-day or every-three-day repeater. But only if it's "must" enough. (See the long answer.)
Long rambling possibly non-responsive answer:
I would categorize the melons differently from the flea medication, because the melons are a “must, IF,” and the “if not” is perfectly acceptable. I must plant melons in those weeks IF I want to grow melons—but it’s perfectly acceptable to not grow melons.
For my garden, I’ve tried to form a habit of doing the “must, IF” early, rather than just in time. Last year, the bed for the bush beans was ready by…late fall? Midwinter? so that when the “must” weeks rolled around all I had to do was poke the seeds in the ground—the last ten minutes or so of a project that had required a few hours of work.
So I didn’t need scheduled tasks for the beans, or the also high priority pumpkins and strawberries, because I was working on prepping beds (and running irrigation line and setting up trellises, blah blah blah) all through fall and winter and spring, and I just kept working on the highest not-yet-done priority. When spring hit, I hadn’t finished everything I wanted, but none of the “too lates” was a surprise, because I had repeatedly bypassed them when deciding on the next priority. No calendar entries, no reminders, just one or two or maybe three projects at a time, then, when one was finished, “what’s the next priority?”
Now, doing work early like this is not natural to me. I didn’t get ahead by working harder—I got there by dropping a whole lot of other garden projects. My 2021 and 2022 garden plans were far less ambitious than usual, and it looks like 2023 will be too, because I decided that I wanted to do (1) less, (2) better, (3) early.
(At least, that’s how I remember my intention. Come to think of it, I’m forgetting that I also cut the priority of the whole garden, along with cutting many other activities, because I decreed that my first personal priority was getting the first draft of my novel done. But the realization that my writing goals required a much simpler garden has resulted in a much better garden. Huh.)
Where was I?
Oh, yes. Melons are optional. I can plan and track them with other work that gets done early or not at all, and thus they don’t need calendar presence.
But timely health care for a dog is not optional. So it would get a popup reminder, every bleeping day, until it gets done. I have too many of these reminders, but so far not so many that I go totally numb to them. I do need to find a way to get more of them done early, before the population of reminders does grow to that point.