Few quick answers:
You can autoload lisp programs, so you don't have to do it manually everytime. (ironically while working half of the lisps I use, I'm loading manually)
Yes, I'd call it an 'easy' modification.
Its possible, but I don't have that much free time to play with:
From each endpoint of the original polyline, find the vector that is tangent to the offseted polyline, resulting in finding the intersection point from where the straight taper would start.
Although looking at the picture the above algorithm may not produce the desired result, because a curve/bulge is used for the taper.
Another easier approach would be to use Lee's Polyline Taper and Polyline Outline, so you could manipulate each start/end segment's width for every polyline and in the end outline them.
And I believe that would produce the desired result.