> 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.