The wrapping concept is best explained as if you took a tube , sliced it down the long axis and uncurled it.
That is you 2-D workplace.
As you mentioned , the job size width is the circumference.
That is determined but the numbers you input when setting up the project
I’m not sure I understand your question about the vectors overlapping and nesting...
The Material thickness being 1/2 the diameter ?? remember that you are working with a cylinder, and if using the center of the material as the Z0, then yes.
Have you looked at Randall’s tutorial ?http://www.222artisans.com/Rotary/RotaryYaxis.html
It’s very good.
Are you looking for something like what I have attached ?
Let me know if I can help further..If you want to send me the file, I can write a short tutorial for you..
Sorry, I wrongly put Paul's name for Randall,,,Both very talented people,,easy to get them confused..