Big pivotal moment is probably the DMCA and the DRM it's enabled, it's really eroded the concept of ownership in both software and hardware (via firmware), to the point where we've completely lost all control over the devices we buy.
These days devices do what we ask when it benefits their real owners, and refuse to do what we ask of them when it doesn't.
It wasn't an overnight thing, but the temperature in the pot has been increasing for well over a two decades and it's getting more than a bit sweaty.
It's not like Doctorow, the EFF, and a bunch of others didn't warn us. They told us this would happen. Like exactly this.
I brought this up all the time I argued with co-workers I advocated for Open Source because I knew where this was headed and every time it played out the exact way this comic did. Now I just post a link to this comic in discussion about these kind of things. https://xkcd.com/743/
I don't think "jailbreak and install your own software on your TV" would be common even without the DMCA...and it would still be necessary, nothing would be stopping the companies from writing these stock software systems.
Active regulation of the marketplace is needed.