Using classic Outlook for Windows in business environments
Thanks, Robert Harris3,
Your post and TomRDRX's post prompted me to do some testing as well. I also have Outlook hooked up to my personal Hotmail account and my work account. I confirm the same scenarios as you: can send just fine if using my work account but experience a crash when sending with the Hotmail address.
Hopefully these consistent symptoms from multiple users will allow them to actually resolve this.