Despite being a forum junkie, I do agree with you. “Better news delivery” is being worked on: whonixcheck Whonix 14 ideas
Whonix 14 should have a more-informed transition process.
Regarding the actual upgrade process: Qubes does not handle template upgrades. Each template is responsible for itself - meaning no guarantees can be made that future upgrades will be any simpler or more automatic. However, your point about being directed to upgrade instructions before actually upgrading is well taken (by me - but I’m not a dev 
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