For what it is worth, one way I think about this situation is "How can I be most consistent [in a world where print is notoriously inconsistent]?" For me, that usually means the following 3 things:
Always let punctuation be included in the effect of a typeform word indicator.
When a typeform terminator is needed at the end of a "typeformed" passage, put the terminator after punctuation UNLESS what's "typeformed" is a title (because titles are really specific serieses of words, which do not include ending punctuation).
Try my best while also knowing that my proofreading and or audience will have a different perspective and will likely find at least one typeform application that should be changed.
So, I would apply the typeforms as illustrated in the following pictures (also in the attached BRF).
–Kyle
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