So I had a brief call with Apple today. Their suggestion was to move everything to one account or the other. Because of all my purchases on my iTunes account, that’d mean moving all my calendars, contacts, photos, and iCloud Drive to the other account. That sounded like a potentially lossy and error-prone process, and wanted to avoid it.
But while I was on the phone with them I thought of another solution: I created a second user account on my Mac, logged in to my iTunes Apple ID as if it were the primary iCloud account, and sent the family sharing invites from that user. Then I fast-user-switched back to my regular account and continued living life as normal 🎉
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