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Assuming the goal is to install clones of Civi + WP + MySQL on two servers (let's call them "production" and "dev" with those roles in mind):

These days, is it better to install first on dev then migrate to production, or is the reverse preferred? Does it matter much?

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This isn't really a question specific to civicrm, but in general unless you never plan to upgrade or do any customization after the initial installation, you'll want to have the dev to production direction set up anyway.

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