Writing as an activity lacks a notion of difficulty. Compare with math, where mathematicians have good consensus on some theorems being easy to prove and others being hard to prove or unproven. With writing non-fiction, we assume topics differ only in time needed, not difficulty
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Also topic difficult is often confused with wrongness of underlying thesis. To use an earlier example, it is difficult to write about "The Problem With Whig Polyannish Economic Optimism" but that's not proof that there are no problems or that the problems are imaginary.
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Relationship to cryptography. It's easier to multiply two large primes than to factor the product into constituent primes. Many contentious topics have this kind of difficulty asymmetry. A thesis being harder than the antithesis, where both are "great truths" a la Niels Bohr.
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Of course, if the thesis and antithesis differ in correctness as well as difficulty, you're in even murkier territory. If the two asymmetries align you get overwhelming ease in one direction. The tough case is the H. L. Mencken case: the false argument is easier to make.
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How did you get better at assessing difficulty?
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by writing a lot
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