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I think most users who request account merges for themselves don't do so primarily out of concern for the well-being of the site as a whole, but so that they can comment on their own posts and on answers to their questions, edit their posts more easily, and (though maybe this is not as much of a motivation) accept answers. Emphasizing these benefits may help encourage merges. Since I think the driving force behind users requesting merges is not concern for "organization and site-cleanliness," I wouldn't expect sysadmins or any other group to request them more or less often than other users.
In my experience, at least on some other SE sites, users who have created multiple accounts unintentionally often follow instructions to use the contact us link to merge them.
