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This might be a bit uncharitable. Psychometricians are looking for items with a range of difficulties that can discriminate at different levels of ability. If the distribution ends up being really right-skewed, it means your test can't tell people apart at low ability levels.
If your test produces a noticeably different curve when test-takers have an hour vs. all day to complete it, "difficulty" becomes "difficulty at high speed." This is a subtle but important difference.
Oh yes, absolutely! Was more reacting to what I perceived to be your argument that test-makers take arbitrary measures to make their tests match a distribution.
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