I still think the answer here is 'never', communities should be as self contained as possible and not try and take over personal lives. To do otherwise reminds

I still think the answer here is 'never', communities should be as self contained as possible and not try and take over personal lives. To do otherwise reminds of those schools that try and punish students (and sometimes teachers) for actions done in their free time; an absolutely ridiculous overreach that makes things worse rather than better. And I stick by that for communities I run. On every site I'm an admin/founder, the rule is that (legal issues excepting), we won't punish you for things done outside of the community. It's not our place to do so, and we have no interest in witch hunting or trying to find reasons to deplatform people for things they do in their free time elsewhere.