I have the task of packaging and shipping a commercial application bundle, which will include:
As far as I can see Python is distributed via a msi file. It seems natural to me that you create a msi installer as well. To create msi files you can use e.g. the Windows Installer Extensions toolkit. If you create your own msi and include the other msi into yours then you will get into trouble to install the pyhthon package during your own msi installation routine since Windows does only allow one installation at a time. The easiest way would be to repackage the python msi into your own msi and distribute this one. You can decompile a msi into a xml file which can be used to create a new msi with dark which is part of the Windows Installer Extensions toolkit.
If you did manage it to deploy the your whole suite via a tar file it should be possible to use a zip file on Windows as well if the pyhthon and your other stuff is xcopy deployable. When you must do some actions like setting registry keys, environment variables, creating shortcuts you should use msi since it was designed for this task. But be warned: Msi is a difficult topic. If you need to get something quick you should check how far you can get with a zip file and some scripts. A msi based installation will make servicing and patching much easier but to appreciate these advanced features you will need to invest some weeks to learn it.