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https://github.com/novoid/Memacs sounds like it might be somewhat related to your goal of making a timeline of your activity.
Maybe org-capture with something like this, then? https://github.com/alphapapa/org-protocol-capture-html
If you're using org-roam already, might be worth looking into delve.
Yes, I do self-host a public instance under https://organice.200ok.ch and use it daily - from my phone and to share Org files with non-Emacs users.
I dont have any comments on clipping, but I use Reverse datetree. It allows you to tweak the tree. Then set org-reverse-datetree-level-formats for only a year and the date. Set up a capture that adds the time.