When you have a multi-machines deployment and you have Portal installed on a separate machine you can not run the python script to scan Portal for security best practices. Although ESRI has a python script for that under the installation/admin directory (Portal). Portal installation doesn't come with Pyhton27. For this deployment scenario, ESRI needs to have a separate Python installation for each Portal version or have a Portal package with Python for installation on a separate machines. ESRI assumes all installations are to be on one machine (ArcGIS Server, datastore, and Portal; the first two come with Python). I have brought this issue to ESRI attention.