Outlook, Gmail, Calendar and Google Assistant

I’ve got myself a nice little arrangement, but I can’t help but think I could be leveraging Google Assistant a little more in my life. I don’t need to do it, but as any self-respecting geek would, I want to maximize my tech leverage.

My current setup is thus: On my home desktop, I have Outlook configured with my Personal and Hotmail accounts for email and calendar. On my work laptop, I have my Work email & calendar in Outlook, Windows Mail for Hotmail and webmail for Personal (Personal email won’t work in Windows Mail for some reason). On my Pixel 4XL, I have disabled Gmail, and I use Outlook for everything, though I do have a Gmail account as my “main” account on my phone.

The end result is a fragmented mess, where the only place I can get a complete picture of my email and calendar is on my phone, since Outlook on my home PC can’t connect to my work account, and Outlook on my work PC can’t connect to my personal accounts. I’m managing with this so far, and it more or less works. Contacts are still a mess (no real sync between Outlook and Google apps like Messenging for example), but I can live with it.

I would, however, like to better integrate Google Assistant, particularly with my calendar. I can see many benefits there. I imagine it’d be even better to integrate Gmail, but I really like using Outlook.

I imagine there are others here with similar requirements, who’ve figured out a better way to configure all the devices in our lives. Any tips?

Ugh, Outlook is so bad.

I’m not sure what I’d do without the search capabilities of Gmail.