It is pretty standard practice now for desktop applications to be self-updating. On the Mac, every non-Apple program that uses Sparkle in my book is an instant win. For Wind
I'd suggest that you package your application with pear and set up a channel. Your users can then upgrade the application through a standard interface (pear). It's not entirely automatic (unless the users have some kind of automation running on top of pear), but it's standard, so any sysadmin can maintain it.