I think an interesting attack on this loophole would be a law that requires that the relevant signing keys/bootloader access be opened 1-3 years after official support for the hardware ends.
Sure this would complicate things a bit (Apple would have to have different keys for different hardware revisions), but it would allow devices to be "officially" jailbroken after support ends.
Like this, I would really support this. However, Apple would probably point out the Third World countries might have more obsolete devices coupled with more oppressive governments and that puts them at more risk or something.
