I would avoid windows (plenty of threads on here will show you why). Install debian, install Kodi, install hass in a virtual environment via the manual method. Should be up and running in an hour or so depending on your technical prowess
Python and HA itself run perfectly well on Windows. However many of the peripheral programs that are commonly used are simply not available on Windows, or work completely differently, so you will spend a lot of time just trying to do many of the things suggested in the forums.
The debian/kodi/virtualenv installation looks good to me.