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You strike me as a user who'd benefit greatly from minimizing tool counts--this is a lot of steps for what a small pocketbook and pen can accomplish.[Also very little can match the pen/paper combo's security levels]
With all that said, I know paper can't grab your attention on its own, for this reason I overlap with tuta calendar (Which should be a reasonable level of security and convenience imho).
When you using that many separate techs, it has to almost feel like the tools themselves require more attention and care than the work you need planned and structured.
I personally use pen and paper predominantly. The tools built up over years, so it is more cruft from time. They mostly work together because it is Caldav from Nextcloud -> Thunderbird or Dax5 + Mobile Calendar app. Just find any of them do not work in quite the way I would prefer. You know?