Google's recent message was more helpful - apparently forwarding emails from the accounts I setup for my kids to my wife's Gmail account triggered some obscure rule that ruined my server's reputation with Google, and I think Google & Microsoft collaborate because the issues cropped up within a week of each other.
The interesting thing was I discovered the Outlook issue by trying to reply to an email sent from an Outlook customer. Yes, my reply to an Outlook customer's email to me was blocked because of my server's reputation.
To be clear, I run no mailing lists nor solicit any business with my email server. I use it for personal use only and my consulting work which involves know contacts. The forwarding I spoke of before is solely to our own personal accounts.
I use Mail-In-A-Box, for what it's worth, on a Linode VPS.