oh, no, don't apologize.  i think you've done a very good job of describing something that works very differently than polygon modelers. 

in terms of the cone vs, cylinder: i do kind of the same thing.  so for a circular skirt i try to work with an actual circle.  it's kind of tricky my way because of how everything works.  right now i "sew" the top, then attach the skirt. i may find a better way to join the two.  for something that's more A line or straight hem skirt, i work with planes and just "sew" them like i did the shirt.  my latest skirt was gathered, so you can still use that method on a loose, flowing skirt.  but i suspect it will work much like a skirt actually made that way and not bell out in a circle.  on the other hand i have a sort of princess dress with a big long train that i made that way.

oh, and LaurieA, i totally understand about Blender.  i think comfort with modeling programs is really individual.  i'd think you could do the same thing in Wings?  so let me see...