The windows installer already adds some contextual menu items but it's horrible. We should do it like winrar does it: have a contextual menu item VLC with subitems. vim has open source code to do that. see: http://cvs.sourceforge.net/viewcvs.py/vim/vim/src/GvimExt/
not necessary for OSX because of the "macosx-autoplay" option (which allows an "always enqueue mode") in combination with OSX's "Open with..." item in the action-menu and CMs.
Additionally, based upon my limited windows experience, we already got something like this there, so is this ticket still needed?