Enabling Microsoft 365 for Email - Have Questions Before I Do This

I have had Dreamhost since 2005, and I have a LOT of email. I’ve been using GSuite to get my email since 2014 (but not via MX records), and I’m moving to a Microsoft 365 Business Premium account. I know how to add the MX records to make the switch, but I’ve not done high level email admin work before (learning), and I’m wondering a few things:

  1. I have several accounts on my Dreamhost email. I think there are 7 full mailboxes and 10 forward-only addresses. I only access 1 on a regular basis. Sounds like I may not want to change where it’s hosted. But I want to be able to send via Outlook365. I guess I could just set up SMTP in the Outlook365 app and not bother with Exchange? Thoughts since I don’t really need full Exchange?

  2. With my current GSuite setup, I can still access my Dreamhost email via webmail.mydomain.com. Will I still be able to do this when I set up the MX records to point to Microsoft 365 instead? (I’m guessing no, but want to verify.)

  3. Any suggestions on backing up email before I make the change? I’ve done a full account backup via my Dreamhost panel, but if something goes terribly awry, I’d love to have email somewhere I can easily restore it. But there’s a LOT of email. Some worth saving, but it may not be possible to take the time to sort 15 years of it out right now, so I’m open to options that might not involve a week of download time or manual copying.

  4. Is there any way to see the size of my mailbox per email address currently at Dreamhost?

  5. Any other advice, best practices, or pitfalls to avoid?

Thanks in advance for any advice you can give! Stay safe, my friends!

To backup your GSuite email, you’ll need to do that via Google. Here’s their doc about the process:

https://support.google.com/accounts/answer/3024190

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