I am not sure I understand your notes re: WordPress.com vs .org. I have a couple of friends who bought their own URL separately but then use the WordPress.com framework to help them build a site without knowing HTML, etc.
But you seemed to note the difference as being URL as well as a shared server vs your own…?
I thought it was more the UI framework allowing non-technical people to create a simple webpage, vs. .org requiring coding skills. Am I wrong in this? Do you have frames and can drag and drop? Or do you outsource?