I use Ruby for light scripting on a Windows machine. RubyInstaller worked just fine and so do the irb shell and my scripts. Dropbox is a web app, so who cares about GUI toolkits? Perhaps you're right that the Python community tried harder, earlier, to support Windows and other non-UNIX platforms. But it's hard to imagine Dropbox actually selecting Python to build their web app for that reason. Maybe in their earlier days they used a hosting service that supported Python but not Ruby, Perl, etc.? Who knows...