Per David Wilcox (who literally uses a different tuning for almost every song) use 4-6 winds on the post so that you are bending around the larger diameter of the capstan. I've done that for years after taking a workshop with him, and now rarely break a string -- even when working through the six tunings that I routinely use for slack-key and other styles.
Tuning up and down is the quickest way to kill the tone of a string, so after repeated changes you may need to change it for new anyway. I have multiple guitars so some of them live in dedicated tunings. But as a string set gets toward the end of its tonal life, I also practice changing between tunings to maintain that skill too.
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