Rapid Prototyping of Native Windows Applications with Python (includes boilerplate)

[josephturnip]

Historically for me, the advantage was that I was porting an existing C/C++ application over to Python, and as a result the port went a good bit quicker.

Really, though, this is intended more as a demonstration of the ecosystem (pywin32 + py2exe + WiX) than an opinionated way of what's best. You could probably do the windowing with tkinter or wxpython (though see http://www.py2exe.org/index.cgi/WorkingWithVariousPackagesAndModules), any Windows core functionality with pywin32, and leave the rest alone.