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Which one of the following is more appropriate?

...offers scope for the theoretical integration of teaching, learning, and development with the culturally new user-generated and mediated contexts.

Or

... by an emphasis on information sharing, collaboration, community building, open data standards, and user-generated and -mediated content and applications.

Clearly, in such a situation, should dash be used for the second word?

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    You are asking about hyphens, not dashes. British sometimes do not distinguish, but in America there are three common types of horizontal-line characters: hyphen (-), en dash (–), and em dash (—). Style guides (such as those mentioned by Dead Rat) typically discuss separately the usage of each of these. – Brian Hitchcock Jun 28 '15 at 14:07
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You've got two different example, one with contexts and one with content, but it doesn't matter. The two compound adjectives mean different things. "User-generated and mediated" contexts means that the users make the contexts but the mediation is not necessarily performed by users. "User-generated and -mediated" context means the the contexts are user-generated and user-mediated.

For the latter, consult your manual of style, either the one you've adopted or the one thrust upon you. I use the Chicago Manual of Style, which is silent on the use of suspended hyphens preceding a word. Amy Einsohn's The Copyeditor's Handbook says this usage is "licit but likely to confuse." I think she's right; be kind to your reader: "user-genterated and user-mediated contexts."

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