I am attending DeVry University's Keller Graduate School of Mgmt.
This is a forum for uses of Canvas and really I don't know how much expertise there is here for Microsoft licensing. But, my guess is that it depends on if you are going to use it as web apps or software download. I believe Word, Excel, etc will only sign in to one O365 account at a time, but nothing should prevent you from logging in and out with different accounts. For Outlook, you would only log into the program with one account for licensing purposes but you can certainly have multiple email accounts attached to it. I've even used Outlook at times for my gmail accounts in addition to O365 accounts.
For web access the same holds true about being able to log in and out as needed to different accounts. Or, with Google Chrome you can create different "People" so you can have windows logged in to the same system using different accounts. Here is a short write up about what I'm talking about https://www.makeuseof.com/tag/chrome-multiple-google-accounts/. I use this feature all the time to keep my personal browsing separate from work. I currently have 7 different persons set up in my chrome browser.
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