I was looking for a
general way how to substitute one glyph with another depending
on context, thus I can't see how there are different problems
in my post? But it's good to hear that others have thought at
least of a partial solution.
Is my guess right that normally the author of a font ought to
provide otf features that can be switched on and off to get
one result instead of the other? That area seems to be utter
chaos in the Calluna fonts.
The output of \sc to produce small capitals depends on the font
and it’s the font designers job to provide a small ẞ (he could use
stilistic sets to let you choose between ß and ẞ).