I think this comic might have been from the era when you did have to pay for new versions of OS X… they stopped doing that around Lion I think in 2011 or so.
The first few iOS updates they tried to charge for as well
I remember because it was laughably easy to just go grab the package file online and “flash” it manually.
I’m not sure what you’re getting at. The versions up to and including Mountain Lion in 2012 cost money on release. If you didn’t upgrade or bought new hardware, you would not have had to pay to upgrade specifically. You could also bum copies off of somebody else… But it did technically cost money.