As for multiple implementations: CPython, Jython, IronPython, Stackless Python, PyPy. What editor do you use? Gnu Emacs with Slime; or, some of the commercial Lisp implementations come with IDE's; and there's work being done ("curl") to make Eclipse work well with Common Lisp. Java has several IDE's, such as IntelliJ and Eclipse. For Python, what I'm told by the Python experts I know is that they just don't use any IDE.
But much of what you're saying above is very much to the point. The comments on my blog posting go into these issues more.