Just my two cents...

I am dev manager in a small development shop. When I started they were switching from Delphi to Java, I had been using python for about 6 months. There's only one other developer other than me and he took to python very quickly, he likes to learn lots of different languages.

Of course it'll be harder when we advertise, but I have a plan. We'll hire graduate Java programmers who don't mind learning a new language. I think that's it's pretty easy to switch from Java to Python. In fact I think that they'll apreciate the
jump, because Python's so much easier.

Also, about the documentation. ActiveState's python comes with a nice CHM file for window's developers, that includes excellent documentation on the python library and the win32 extensions. Unfortunately, third party extension's documentation doesn't "transparently integrate" into python's documentation because there's no standard IDE or help system.

But still there's plenty of help from google searches and the #python IRC channel and Open Projects Network.

And finally GUI support. One of the unique(?) features about python is that it doesn't have a standard GUI library, Delphi has VCL and CLX, Java has JFC and swing. Python's standard has been Tkinter, but there are still lots of other GUI toolkits for python (wxPython, PyGtk, AnyGui, DynWin, FxPy, PyAmulet, PyFLTK, etc....). The graphics toolkit is seperate from the language.

Anyway, this is good because it lets the language be moreportable, but it's bad for the VB developer guy who wants to try out python. This guy wants a single standard library for everything, that everyone knows, a full IDE with drag and drop form design and CVS support, and glossy magazine's with third party add-ons in them and all that good old commercialism added value.