My two cents after reading this whole thread:

like it or not, portupgrade is currently the "official" tool (it's in
the Handbook and all other docs).
So in my view, this is what needs to be done:
a) select a new "official tool"
b) create or update said tool so it is working to 95% of all the wishes
c) update all the documentation pointing to this new tool, and set a
warning ("the old tool, portupgrade, is going away in X years")
d) wait X years
e) remove portupgrade

As Doug wrote, change is hard. But there is a difference between
change because all other options has run out of time, and planned
change.
We can make it less hard, at the cost of a longer timeframe.
-- 
Regards,
Torfinn Ingolfsen,
Norway
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