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It's a type hierarchy misaligment (one item has 1 pin, one item has multiple territories) - do you want to file an issue? I haven't seen any on this particular issue. I can also do it for you if you'd prefer that
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not the easiest thing to fix, but:
crossposted items should be pinnable in all territories have been posted to
That is a literal user requirement, and if you file it as an issue (and explain why!) then you create awareness to your requirement and the team can pick it up.
Yes. There's a check for whether there's crossposting and if so the option isn't available.