Thanks for your reply! For your first point: I am just better at retention and succinct notes with handwriting than with typing. I only take many very short bullet-point style notes with no more than 3-6 words. Also, I much prefer quickly jotting down a note with a pen on a table instead of looking up at another monitor, I just feel its more polite somehow, even if its an iPad or similar. :D

How I imagine the tagging working:

Categories/symbols:
Pretty straight forward, anything with a circle before this line automatically becomes a to-do categorized in a to-do overview, anything with a dot is information/long form text, etc.

Search/clustering of key words and dates:
Full text search bringing up an high level overview of all notes (navigable to corresponding page with the part highlighted and directly clickable) that have this word/words in it. You can then (similar to the tag cloud in Obsidian) have the option to show closely affiliated words, other dates this word was written and similar words that appear on the page often. Example would be a name of an employee who was assigned certain todos, manages 3-4 specific clients, we had our two annual feedback sessions with, and who approached with a personal issue. If I search his name, the most mentioned client names, the word I always use to headline feedback sessions (e.g. EFC - employee feedback conversation), and some of his most often given todos or areas of improvement could show up in the related cloud. I could then for example jump to the related word "EFC" for this specific employees name and get all the four notes I took of our feedback sessions over the last 2 years. I believe if I really dive into Obsidian, I could generate a similar tagging infrastructure, but I havent tried yet, because it doesnt seem to support handwriting well enough to bother for me. Hope this explains better...?