I've tried it a few times but it doesn't work for me because of your third point. I can't maintain a TODO list and I've always had mine grow too big. I end up having to drag 5-10 things to the next day every day after a month or so. I know it's because I'm horrible at prioritization and I do best when given a list of crap to do and can pick and choose what I feel like doing when I feel like doing it.
I use a big whiteboard calendar for my most important deadlines, bills, and appointments. I use a calendar app for recurring events. Then I use Obsidian to dump thoughts, lists, any random crap I think of that I can search through.