> The clearest sign a tool is serving you is that you stop noticing it—it becomes invisible. You don’t celebrate its flaws because you’re not turning them into a hobby, rather you just get mildly annoyed and route around them.

I think this is more dependent on the user than on the tool. Surely, different tools will attract different users and we can probably measure strong correlation.

I also think this position lacks balance. Your tool is never perfect, sometimes you realize you could improve it, and you should balance implementing the change with the effect it'd have on your habits. Sure, the longer you use your tool, the smaller those changes are, but your usage evolves throughout your life, and it's only natural that your tools do so to.