If there is anything that I can personally do to reassure if needed, please feel free to contact me directly. Your advocacy within your company was a wise move, and your company will see benefits sooner because of your efforts.
I am truly sorry for any confusion on the message. There have been a lot of moving pieces this past year and a great deal of effort went into crafting information that would be encouraging and firm without being alarmist or inconsiderate. Everyone has done their best to communicate directly on the future of Python 3 and plans to wrap up CPython core developer work on Python 2. We will continue to iterate on communicating the specifics.
Yes because technically Benjamin could accept a fix for an earth-shattering bug and thus the mechanisms for handling such a case should probably be left around until 2.7 is converted into a git tag.
Seconding @nedbat; the End Of Life date is and was a useful way for people to talk to their stakeholders about the continuing risk of continuing to use Python 2, the same way a “news hook” makes people pay more attention to any advice of continuing relevance.