Questions
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Would you recommend changing image file names retroactively?
Generally speaking, in our experience, it's not worth it to take the time to change filenames (and thus change URLs) unless you absolutely have to. If you're still using the same CMS, then just changing the URL might not be worth it, as you have to take time to set up a 301 redirect from the old URL to the new URL. What it would be worth it to do is to go with a flat file structure, such as domain.com/category/page or domain.com/page/. In the long run, you won't generally have to change URLs in the future if you move to another CMS. If those pages are ranking well with the current URL, you may not want to change the filename. But, if they aren't ranking on the first page, it should be fine to change the filename. Don't forget to set up 301 redirects from the old URL to the new URL.
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