There are software companies that do this, and usually the updates are worth the monthly/yearly fees. But try telling a PHB that! On the other hand, when they do get something for free, they can't understand why it doesn't have all the bells and whistles of a paid product. I actually had one boss complain that the free phone conferencing I set up "charged" for the phone calls to the conference number! And that it wasn't video (she didn't have a camera anyway). I am soooo glad I am retired.
My boss once thought this same thing was a good idea. Until I made a boneheaded move of telling him that Linux is open source and thus free. I still beat myself up for not letting him get conned like the ignorant pile of excrement he is.
This reminds me of those scameriffic "phone rental" companies. The (usually elderly) client thinks they need to keep paying these people to keep their phone service, but in reality, and all they're doing is renting the physical phone for hundreds of dollars a year.
RMS (Richard Stalllman) has a gripe at arstechnica, about Canonical grabbing every desktop and Google search, etc. under Ubuntu, for later sale to marketers (Amazon, etc.). Gives one pause. Convenience trumps security and privacy. We'll bite every time! Smooth, guys!