The first bug is that descriptions interfere with the counters, resulting in the peculiar behavior demonstrated in the resulting PDF. Unless I'm mistaken, I think it happens because the head of the description is evaluated twice, thus incrementing the counter twice---at least, that's the only explanation for how the number is incremented by 2 each time. Further, this issue seems to persist whether we're using macros or writing \incrementcounter directly. The solution is to either make sure that the head of descriptions is evaluated only once, or document that text placed as the head of descriptions is meant to be evaluated twice, if there's a good reason for doing so. Of course, this silly example of incrementing counters can be subdued by placing the \incrementcounter directly in the after option when customizing descriptions. But it demonstrates the issue. I've tried to make the examples given be as varied as possible, demonstrating the different ways in which descriptions interact with the counter. The second bug is that descriptions, or at least that's my intuitive expectation, shouldn't interfere with the bullets of items. I expect that the bullet stays where it is, and the description is placed next to it. But what happens is that the bullet is shifted to the right, making it overlap with the description's head, which isn't pretty. ConTeXt version 2024.1.24