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You would normally handle this with multiple relationships on the "Relationships" tab.
I suspect an unspoken requirement is that the Chapter relationship should be on the "Summary" tab. You can do that with the Relationship Block extension, perhaps paired with Contact Layout Editor to position it where you want.
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If you're talking about CiviMail message templates I think this is very similar to this question, maybe even a duplicate. You need to use {capture} and then put the captured variable in your if statement.
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Did you try 'Synchronize Users-to-Contacts' from UI? You need to make sure you have unsupervised dedupe rule for individual set to email only before running 'Synchronize Users-to-Contacts'
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