> What baffles me is that so many people treat that friction—the effort of working around a tool’s limitations—as the “fun” part, and then advertise it as evidence that the tool is great.
I think it’s fine if that’s your hobby, but I agree that in a professional context one should be much more critical of their tools. Even asking “why do I need a tool for this at all?” will reveal shortcomings in processes, data structures or other tools that will reap much greater rewards if effort is put into fixing those instead of optimizing use of a quirky tool.
Theoretically yes, but in reality I have found that often it's much easier to just fix something locally or with a workaround rather than jumping through all hoops required to get somebody in another team or even another company to understand and agree with you on your (or your teams) issues, let alone fix them in a satisfactory way.
I think it’s fine if that’s your hobby, but I agree that in a professional context one should be much more critical of their tools. Even asking “why do I need a tool for this at all?” will reveal shortcomings in processes, data structures or other tools that will reap much greater rewards if effort is put into fixing those instead of optimizing use of a quirky tool.