Yeah this is my question. My Kindle has been in airplane mode since the day I bought it.

As long as I can still keep loading books on it over USB, and it's just their DRM ecosystem that will stop working, that's fine with me.

But if they are aggressively bricking the units, if I accidentally turn on wifi by accident and it just completely stops working, I will be extremely pissed.

Jailbreak it now to avoid the risk.