I need to extrude a complex 3D surface to another even more complex 3D surface, and the extrude must have a 10 degree draft. The result must be solid.
Lofting/Boundary is out of the question, as I need it finished still this year
...But the draft doesn't work (works only for a small segment), as visible on the pictures
Adding extra segments goes shenanigan mode
Although the source and destination surfaces are complex, the problem seems pretty much like another SW's fussiness
You'd be way better off to just use surfaces. You're trying to specify a more difficult way to do it because I'm guessing you don't understand surfaces very well, and you're afraid of working with them. Since you already have some surfaces, and it's not clear that the method you're trying to force on the model will create something compatible with what is already there, I would just use surfaces. You said there is something "complex", but this is all pretty simple, until you start forcing a solid work flow on it.
Attached is something to get you started.