I used to have a really nice system for writing bullet points that described the item: dot for new item, arrow for pushed to next day, check/tick for done, star for important, cross for cancelled, etc etc. I just really wish all that stuff would appear automagically in my Emacs org-journal folder. I haven't tried an iPad pro for writing, I just have the 10.4" normal iPad and don't like trying to write on that. It's compounded by my preference for super-fine pens, so tablet-based writing just feels so clunky.

I'm not sure what point I was trying to make there. Maybe my need for more coffee this morning?

I pretty much moved over to a 12.9" iPad Pro + Pencil when they first came out. It replaced my "system" of doing derivations on the blank side of the leftover cover pages from the department printer. They were then "filed" into a giant pile in the corner of my desk.

Some part of the chaos of this system was deliberate - unbound sheets that you only write on one side of are great for derivations as you can lay out many of them on a desk to see what you wrote a few pages ago. Still the iPad is a vast improvement for me, even if you can't see everything at once.

Also I don't think the iPad Pro would improve things for you, it's great if you're used to the wonderful Bic Cristal, but you definitely won't get the precision of a super fine pen, though maybe the newer generation is better on that front.