Apparently with Snow Leopard, due to rewrite of Finder in Cocoa and removal of Contextual Menu Plugins, it is no longer trivial to do either badging nor contextual menus, however Dropbox seems to both add a contextual menu in the managed folder, and add status badges.
Is there an open source project that managed to solve this problem?
It's been years since this question was asked, but here's (almost) exactly what you were asking for: FLOSS that implements badging and contextual menus, but only for Lion and Mountain Lion (but I'm sure it wouldn't be too difficult to adapt it for Snow Leopard if still needed).
Liferay Nativity provides a scripting bundle that will swizzle the relevant Finder methods and a Java client for setting the icons and context menus. It also includes equivalent projects for Windows and Linux.
The project is open source under LGPL, so feel free to contribute any bug fixes or improvements!
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