Microsoft calendar sharing

As Microsoft migrate Hotmail users to their new Outlook.com infrastructure calendar sharing has stopped working (or is, at best, intermittent). I spent hours today on Microsoft chat support and got two different stories from two support staff. One said that when the migration was completed (by the end of the year) everything would be wonderful. The other said that calendar sharing in Outlook 2016 was no longer supported.

What used to work was - my wife and I each had a Hotmail account and could read and write each other's calendars. I used Windows Live Mail as my interface. With the Hotmail to Outlook migration calendar sharing in Windows Live Mail no longer works. So I bit the bullet and subscribed to Office 365, using Outlook 2016 as my mail and calendar interface. That worked for a while, but now I can no longer write to my wife's calendar (perhaps her account has just been migrated?). I now have more success accessing our Microsoft calendars from my iPhone than I do from Microsoft applications or web interfaces. And calendar entries my wife put in her phone last week are in my diary, but not entries she added yesterday.

Has anyone else experienced this issue - and have a solution?

If we can't fix this soon we're going to have to upgrade to paper diaries and talking to each other.
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