Erin, I see your point, although 19 and 20 do seem to be closer together than previous major version changes.
People like me can't upgrade to the new SSMS versions nearly as quickly as we want to or MS would like us to, because we are waiting for add-ins to be updated.
Maybe an answer would be to make data available to add-in authors about potentially breaking changes under NDA (with the understanding that the specifics may change during the development process) so that they can get a head start. Of course, they would need to come to you, because you can't be responsible for knowing about every third-party add-in. But some official way for them to register for such an update information distribution list would potentially be useful. Maybe there is a similar program for Visual Studio add-in developers that could be copied, but I really don't know.
Thanks for listening!