Last fall I kept searching college application timeline senior year because I felt weirdly behind by September. The one thing that actually helped was making 3 deadlines for every school instead of 1: my draft deadline, my proofreading deadline, and the real submit date.
Example: if a deadline was Nov 1, I set Oct 10 for personal statement edits, Oct 20 for supplement drafts, and Oct 25 for final review and portal checks. That buffer saved me when a teacher submitted a rec late and when I had to rewrite a supplement.
Also put scholarship and honors deadlines in the same list. I almost missed one because I only tracked application deadlines.