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Recently, I created the tag as there are many questions regarding it. I went ahead and edited a few questions to include this new tag. Would it be a good idea to retag all the 82 (and counting) results that include the phrase HR diagram, or should we keep them as is and let new questions trickle in with this tag?

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Manually retagging more than 4-5 questions in a big batch is discouraged because unfortunately it clutters the active questions feed. But if you want to slowly work them in over time, I don't see anything wrong with that. Since you use an abbreviation you should probably create a tag excerpt that describes the tag and spells out Hertzsprung-Russell diagram.

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    $\begingroup$ Definitely agree with what called2voyage said. I think typical advice is to also do those batches on weekends where activity is low, meaning that you're not taking up space from as many recently-active questions. $\endgroup$
    – HDE 226868 Mod
    Apr 28 at 15:03
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    $\begingroup$ @fasterthanlight here's an example. I tried to do it in a few "waves" rather than all at once for the reasons mentioned above. I found it helpful to work in chronological order (use "newest" when doing searches) and to keep a list of which posts were modified, just in case it's necessary to reverse something or make a further change in the future, as well as to keep track of progress and to allow people to yell at me if I did something wrong and to defend myself if they say I did but I didn't :-) (It's a big undertaking/site impact) $\endgroup$
    – uhoh
    Apr 30 at 1:12

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