Chatbox is a free OSX application that adds project collaboration features to Dropbox. It adds the ability to leave comments on or chat in real-time about about particular files and folders in Dropbox. Everything is stored in Dropbox, so you don’t need to register an account with Chatbox.
Chatbox was created by the team at PandaDesk, which offers a more featured collaboration platform, including status updates and tasks and milestones. PandaDesk integrates with Dropbox.
If you need something more cross-platform and business ready, Box and Huddle are enterprise-grade file storage and document collaboration services. Huddle has a special emphasis on project management. You can read our story on AKQA’s Huddle deployment here.
Also, Google Docs recently revamped its comments to improve collaboration.