Is it a good idea to rel=canonical dozens of old outdated pages?
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we have dozens old outdated manual pages that still need to be up, but have terrible code issues (they're exported from word) and no image tagging, etc.
there are new pages in place, so should i rel=canonical to the new pages? will this transfer any link juice to the newer, more seo-friendly ones?
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If there are newer pages in place, and the newer pages cover the same topic, then yes you should canonical the older, outdated pages to the new pages. I would normally suggest to replace these older pages but you shared they "still need to be up" so the canonical tag would be the next best solution.
Using the canonical tag will allow most of the link juice from the older pages to flow to the newer pages.