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@daughter@husk.site @sean both gmail and outlook.com can be problematic, not really in terms of migration but dealing with them as recipients. So much bullshit done in the name of "anti spam". However it isn't an insurmountable problem, as if it gets worse they'll risk regulatory smackdown (at least outside the US).
I've self hosted my email for longer than gmail has existed. So far, if you make sure you've got valid SPF, DKIM and DMARC you're fine. Maybe make sure PTR record matches MX just in case.