It turns out that the ToolTipcomponent will not display a tooltip a second time if the first timer is disabled. I believe this is a “feature” and not a mistake, but I agree that this is not the expected behavior for many people. This was reported by Microsoft , who believe that it is "too big a question to invest in fixing it."
The answer to this similar question offers some possible workarounds, although I personally have not tried any of them, because I never need a hint displayed for this for a long time, which it has been timed to.
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