> I'm not sure why it's "run upload" instead of just "upload"
pysetup has actions and commands.  Actions do stuff on the Python installation: “pysetup metadata foobar” prints metadata, “pysetup remove foobar” uninstalls, “pysetup install foobar” fetches from PyPI and installs, etc.  Commands are like distutils commands, they work on a project in a source directory; for namespacing reasons, they are subitems of the run command.  (I’m working on documenting that.)

> Apart from that, this looks like a vast improvement to me.
Good!  Adding the easy keyword, as it’s not hard to implement if one understands how upload works, or someone could add tests without much difficulty.  I may get to it myself shortly, it will make a nice change from bug fixes and improve my karma :)