Best practices for monitoring the need for future updates on a theme that I developed?

If the theme repository is anything like the plugins one, content that hasn’t been updated in a while gets hidden, even if it still works. Its probably a good idea to check themes and plugins at least once a year against the latest version, update their meta information, and check them into the repository as an update, even if no functional changes needed to be made. It lets wordpress know you haven’t abandoned it.

(As I have a few plugins in the repository I should really be following my own advice here, but…)

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