I have gone that far sometimes just for the sake of completeness, to be as sure as possible that I'm not losing something that's a breakpoint in how you organize things. But I learned that if a method relies on being way deep to be functional, chances are it's way too rigid and impractical. I do engineering projects that require hundreds of doc pages, and obsidian with markdown, a simple table of contents and a file browser just collapses all back again to manageable levels.