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I encountered this command while reading a piece of fiction:
休んでなさい
I learned that the pre-masu form is used with imperatives using なさい. So, I would have expected 休みなさい. But, here, the て form is used.
Why is the -te form used here? Is there a difference in meaning or nuance between the -te form and pre-masu form when used with なさい? Is this usage a specific and irregular form used only with the verb 休む, perhaps due to the already pre-existing fixed expression おやすみなさい?
I don't think this is so much the difference between the two but rather a combination of the two. Here the て-form is used in the continuous sense, 休んでいる, and the なさい is simply applied to the end. In this case it is telling the person to continue to rest, instead of to rest from here on. A more intuitive reading would be like "Just relax. Stay there." This type of request/command comes up here and there in various Japanese phrases. For instance いい子にしてろ (heard in a manga once) "don't act up" or commonly 待ってて "wait there for me." It doesn't carry over to English easily, but once you get the concept it comes quite intuitively.
