Long story short.....
I installed Office 365 on my new computer. I had the same error occur multiple times when starting Outlook. MS support confirmed it was a corrupt profile. After working on it for quite a while I am convinced that the corruption occurred when adding the outlook.com email address. Outlook is now running fine with my 3 email addresses, and not my outlook.com email address...which is fine.

I used the import function to import calendar and contacts from the pst file of my Office 2010 installation on my old laptop. I also used the import function to import a bunch of "saved" emails. I think they are all there.

In Outlook on my new laptop both the calendar and contacts say "This computer only"
How do I get calendar and contacts to be in the cloud? Accessible via live.com, I assume.

Once I get the contacts and calendar successfully "in the cloud", is there an Android app to access them? Or do I need Outlook for Android?
My email is IMAP, so I don't think I need Outlook for Android to read the email. I already have an app for that.

Thanks in advance!