I've got a project with 92 Python extensions written with Boost.Python (but I don't think that detail matters here, hence my more generic title) for which PyCharm fails to generate skeletons. My suspicion is that PyCharm tries to import those modules and that it fails because each of them requires some specific module of my project to be loaded first, a fact that PyCharm can't guess. This intuition of mine comes from the fact that WingIDE successfully scraps those modules but then I had to specify what they call Scrapping Helper Snippets for each of them. Those are small user-defined Python snippet that Wing executes before attempting to import a module. I used that feature to put the necessary imports for my compiled modules.
Does my reasoning make sense? If so, it would be nice if PyCharm had that feature offered by WingIDE.