I think a problem that's coming up now is that the lines between proprietary and free software have blurred. The FSF movement made sense in the old days when we had to pay a one-time cost to buy a CD with software on it. Today because everything is delivered as a service, it becomes very difficult to distinguish the software from the service itself. We're not just paying for the software anymore - We're also paying for continuous software updates, security patches and the ongoing management of underlying hardware infrastructure... The money has to come from somewhere.
I just don't understand the purpose of the FSF anymore... For the same reason that a 'Free Hardware Foundation' wouldn't make sense - You have to pay people to look after the software infrastructure in the same way that you have to pay people to get the silicon out of the ground to build your hardware.