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You'd think that removing the bold word would be fine, since the structure is obvious even without the bold. And yet the sentence sounds bad to me when I delete the bold; any idea why I prefer to keep the bold?

  • work that relates to the issue of “good design” and to the issue of why—or if—certain properties hold of a well-designed system

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Hi, Andrew,

You'd think that removing the bold word would be fine, since the structure is obvious even without the bold. And yet the sentence sounds bad to me when I delete the bold; any idea why I prefer to keep the bold?

  • work that relates to the issue of “good design” and to the issue of why—or if—certain properties hold of a well-designed system

I think that is because of the repetition of "the issue." Actually, you would tend to prefer for "to" to be repeated even if there were another noun phrase, and this would be to ensure parallelism after a prepositional verb like "relate to":

  • work that relates to the issue of “good design” and to the question of why—or if—certain properties hold of a well-designed system

Here's a similar case:

  • work that refers to the issue of "good design" and to the properties of a well-designed system

Here it seems to me that the second "to" is even more necessary for "the properties..." to link with "refers to" and not with "the issue of..."

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