In my first job, my supervisor gave me a Day Timer binder and set of pages for it and I very dependent on it within a few weeks. That thing was always with me and I was a little terrified that I would leave it somewhere. If I were hit by a bus and they gave that book to my replacement, they would have no problem picking up where I left off.

Then I got a series of Palm Pilot devices and left the paper behind. It worked pretty well for me and the grafitti handwriting system was ingenious. Aside from my contact list being duplicated a few times a year, I didn't really have any negative experiences.

Then smart phones hit and even though they can do everything any electronic organizer ever did for me, I've never been as happy with them.

I'm seriously considering buying a paper planner again. Shared calendars is the only thing blocking me.

I love Obsidian too, but for me it's just a place where I park notes for future reference. I don't actively use it.

Writing by hand has some advantages and writing by keyboard also has some advantages. Using note-taking app or similar software is very convenient and useful in some situations.