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I agree with others that conceptually this is totally an index, I've not seen a TOC that remixes and reshuffles duplicate targets according to categories, but that's pretty much exactly what an index does. So this is basically trying to do something a TOC doesn't, and to make it behave in ways the user doesn't expect.
Finding workarounds feels unfriendly to the reader. I'd be confused why I tapped an empty space and it took me anywhere at all, and I'd be confused if I tapped a labeled entry and it took me nowhere. Actually in both instances, I'd wonder why that was selectable at all. Basically, even if it worked, I don't think you should do it. IMO of course.
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