"python.exe has stopped working"

@Scott thanks a lot for reporting this!

The log error that you see is harmless, it’s seen before. However, your issue is likely related to this one: KA LITE Server doesn't starts on Windows 10

Would you be able to investigate the error by trying out if 0.17.0 works for you? It’s available here:

http://pantry.learningequality.org/downloads/ka-lite/0.17/installers/windows/KALiteSetup-0.17.0.exe