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I'd like to say the following and I'm wondering if I should keep the hyphen after "ground":

Ground- or boat-based observations are difficult.

Since the individual pieces pieces of that sentence would be hyphenated (i.e. "ground-based" and "boat-based"), I'm wondering if the "or" in between the two makes a difference. Thanks!

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Yes, you should keep the hyphen. This is called a suspended hyphen. It's often omitted, but it's correct (and less ambiguous) to use it.

If you want to avoid the suspended hyphen but also avoid ambiguity, write out both terms in full, i.e. "Ground-based and boat-based observations are difficult."

Alternatively, reword the sentence entirely to avoid the repetition, e.g. "Observations from the ground or from a boat are difficult."

Sources: http://editingandwritingservices.com/suspended-hyphens/

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