> pysetup run upload -f dist/spam-0.2.tar.gz -f dist/spam-0.2.exe

I'm not sure why it's "run upload" instead of just "upload", but maybe that's the convention in pysetup.  Apart from that, this looks like a vast improvement to me.  As far as not supporting globs goes, I guess I don't really care either way.  If globs aren't supported, then I'll probably end up globbing somewhere else (or constructing the full upload list in some other automated way).  The motivation for the complaint is that too many things require manual interaction; I'm not going to use a new, easily automated utility manually. :)