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Apple can't really keep vulnerabilities in iOS even if people demand jailbreaks. It's their obligation to patch them whenever possible to avoid third parties using the same hole to do something malicious.

Except Apple hired Comex, a well known iPhone hacker, to improve security

When it comes to Apple, I seriously doubt it.

If that were the case, why wouldn't they make it easier?

They don't trust Cydia, which is understandable.

That's completely contrary to the idea that Apple is deliberately letting people circumvent the lockdown, though.

2 major reasons:

The content industry

Segmenting markets geopraphically

Marketing via nerdsniping. http://xkcd.com/356/

It has to be a challenge to make it interesting.