The thing with the user guide is that people just don’t seem to find it, even though it is right there on the desktop. I think the best way to address this would be by offering a quick visual wizard-type tour on first launch, similar to how Apple introduces new features.
A version of that concept could be implemented very easily with a basic message box at first launch saying “Welcome to Haiku! Would you like a quick tour of the system? You can always view it later by double clicking the icon on the desktop.”. If the user clicks “View Now”, it would launch the quick start guide in the browser.
As for Tracker and WebPositive, I think so far every reviewer has ultimately figured them out without too much effort, which unfortunately cannot be said of the application menu.
Just making a button say what it actually does can hardly be called dumbing down the interface. But it would dramatically improve clarity. I’d say the best user guide is the one the user never needs to read.
The only application I would really consider renaming would be PoorMan. Calling it “PoorMan Webserver” would make its purpose immediately obvious. Some reviewers could not figure out what it is supposed to do, even after launching it and playing with its settings. Most other programs are usually fine in that regard.