Holy cow, I wrote a book!
Commenter Kevin Dente asks,
"Is it possible to put a folder on the
Start Menu Pin list and have it cascade?"
The last time I checked
(which was back in Windows XP),
the Start menu pin list was a list, not a menu.
(Specifically, a list view in tile mode.)
When you click on the icon, it launches.
There is no code to say "Oh,
if this flag is set, then let me
draw a little menu arrow next to the item,
and if the user clicks the arrow,
bind to the target of this shortcut, enumerate its contents,
and create a menu from it."
features don't exist by default; somebody has to implement them.