"2. Htest's for GrepDialog, outputwindow, configDialog and Filelist are not progressing because of assert statements in macosxsupport.py."

The asserts are to ensure that none of the Tk-variant tests (isCarbonTk(), isCocoaTk(), et al) are called before _initializeTkVariantTests(root) has been called.  And _initializeTkVariantTests can only be called after the initial calls to Tk have been made to create an initial window environment; it's only at that point that we can call Tk to enquire what variant of Tk we are running under (macosxSupport.py:28 and 33).  _initializeTkVariantTests is called from macosxSupport.setupApp which is called from PyShell.main.  This is fine for normal IDLE startup but it doesn't take into account the module level tests.  Ideally, you do want to have run _initializeTkVariantTests before running GUI tests so that the behavior is properly conditioned on Tk variant type, so stubbing out the Tk type with macosxsupport._tk_type = "other' is not desirable.  Perhaps the best way to deal with it is to create a common GUI test initialization function that is called by all of the GUI tests; the initialization function would be responsible for creating the Tk() root, calling _initializeTkVariantTests, and any other common steps that might arise.