Whonix 12 -> 13 in-place upgrade was too demanding for users indeed. A major upgrade that happens during regular apt-get dist-upgrading, apt-get advertising the apt-get autoremove feature and at the same time that autoremove feature breaking Whonix installations for users who did not notice there are instructions for Whonix 12 -> 13 upgrades.
If Whonix 13 -> 14 upgrades do not introduce such breaking changes, then that should be fine.
I like the idea, but I'd avoid implementing it myself due to time constraints unless Whonix 13 breaking changes are required. It's because some items on the roadmap to Whonix 14 are really, really time consuming.
roadmap to Whonix 14:
It would be awesome tackling the "missing project news tool" in a later release of Whonix. Actually the issue goes beyond Whonix. It's a general Debian or Linux distribution issue. For example, it would have been great, if Debian had notified us of CVE-2016-1252 using such as popup so people have a chance to upgrade from the vulnerable apt to the patched one more cautiously, right?
@HulaHoop and me have been working on a concept for such a tool. The proposal draft is here:
It would be great if you'd join our efforts!