I decided last week to move off of iOS and picked up a new Google Pixel. My Google login account is a paid Google Apps account associated with my primary email address. I no longer use Google Apps for email/calendar, having switched to Office 365. For a variety of complex reasons, I'm not able or willing to consider switching back, so please don't suggest it as a solution. I keep the Apps account because there are many other Google services I still use that are associated with that Apps account, while the MX and related records point away to Office 365.
However, apparently Android does not allow you, at the system level, to login to two accounts that happen to have the same username. I have a Google Apps account with my primary email address, and that's successfully logged in. I try adding an Exchange/Office 365 account but get an error saying I already have an account with that username.
Now day-to-day, I couldn't care less because I use the Microsoft Outlook app for my email and calendar on Android. I don't use the Google-provided email and calendar apps. However, it seems Google Assistant can only utilize calendar data from accounts logged in at the system level, and the Outlook App only syncs contact data back to the system.
Google Assistant, it seems unless I'm mistaken, can't be configured to pull calendar data from other apps.
And I can't login at the system level with my Office 365 account.
Change the username of my Google Apps account. Not even sure if this will be possible, but I suppose it's an option.
Sync my Office 365 calendar to Google Apps so Assistant will have the data available to it. No idea what tools can do this. I know I can share calendars with Google Calendar via ICS, but Google only pulls for ICS updates once or twice a day. I need my calendar to be live. I would need a solution that is web app based; if I have to depend on desktop Outlook plugins, I can't expect the calendar data sent over to Google to be current when I'm away from desk (an astronomical percentage of my time). Note that my Outlook calendar is broken into two different calendars: the primary one, and a second that gets fed automatically via ICS from Kayak (my travel calendar). I have no way to consolidate that so it's all on one.
What else can I do? What options am I not thinking about?
Please, help me through this!