I think you need to have a clear separation on what you're trying to achieve. From what you've written, I get the sense that you're combining documentation, wik

I think you need to have a clear separation on what you're trying to achieve. From what you've written, I get the sense that you're combining documentation, wiki and your personal notes together. For example, code documentation is very subjective. I'd combine code comments with readmes and potentially a separate wiki. All depending on the complexity of it. For personal notes like reminders or thoughts, there's no need to keep it up to date. It's ordered by date. And when I need it, I roughly remember when I wrote it. If something needs to be updated? Write a new entry today. I use pen and paper for this. This is also where I sketch one-off diagrams and the like. Separately, I also have a personal wiki for things I learn or teach among other things. Since these are limited in numbers and are quite important, keeping them up to date is not a big task