Maybe I have just been lucky. That luck will probably turn around now that I was all snarky with you!
Most of the problems I've found seem to come from misconfiguration on the receiving end. I've recently had to set my SPF record to softfail because several universities that work with (that both use Office365) are consistently checking the sender's SPF records against one of their own internal relays. So every single email from an outside domain that has a SPF hard fail record is sent to spam. After I and the faculty at the universities talked to the IT department, the proscribed course of action was for them to turn off junk filtering in their email client. They insisted that the obvious screw-up that was evident in every message's headers was just as they had intended it. (This happened at two different universities.)