How to prepare images for a layout width change?

You are almost certainly going to need to write a set of scripts to accomplish what you are looking to do. The first step would be get all of them imported as attachments.

You’ve got a great set of specs for those scripts so the next step is to write each of them (actually, each of your criteria look like they could be a different question here on the site.)

Here’s the list of image handling functions in WordPress; you’ll need them to be able to write these scripts. Check out the attachment and the low-level image handling functions.

P.S. If you want to over the next week or two add each of your criteria as it’s own question complete with a well written title and enough background in the text of the question then I (and others) can answer each question with a specific code snippet and we will have created a great reference for each of those questions that can later be more easily found via Google. And you can even link this question to those new questions in an update.

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