Thanks TomRDRX,
This is precisely what happens in my case, with several additional points that are perhaps noteworthy.
I have a personal account, and work (university) account. When I log into the work account, I can send emails without problem.
If I try to send from my personal account, which is @hotmail.com, hitting "send" produces the hourglass (hanging/waiting/in progress) symbol, and crashes Outlook in about three seconds. This applies regardless of whether I am logged into my work account or personal account. As long as the "From" box shows the hotmail address, it will crash upon sending.
As you write, merely changing the "From" dialogue box, even before writing an email or pressing "Send," will immediately crash Outlook. It makes no difference if I change the "From" field from personal to work, or vice versa.
There is another odd thing. Even when I am signed into my work account, if I hit "File" (top left) and look at account information, I now see my hotmail address at the top connected to Microsoft Exchange. I toggle to change to my work account, the one that still can send emails. But when I go back to send an email, it still shows as "From" hotmail. And when I go back to "File," the Microsoft Exchange options have reverted back to my personal hotmail account, even though I had changed it. The change doesn't stick. As long as the "From" box shows the hotmail account, Outlook crashes upon sending.
I'm not sure how to get back my work account in the default send box, but perhaps a reboot might work.
There was an update in the past hour, but all problems remain the same at the moment.