As someone affected by this:

-The old kindles are great products that last a long time -I don't expect Amazon to support them forever, but kindasorta bricking them on their way out is a dick move -Jailbreaking is straightforward but this probably hits older people who are not very tech-savvy the most. Like quite a few others here, I too have an elderly family member who I had to help resolve this

I feel there's gotta be some compromise between letting old electronics age gracefully so they don't occupy landfill and a company's need to support aging products over a long time... though I'm not sure what's a good model.