Finally this thread is back on topic!! Good lord people!!
I agree with castlesteve. Could someone "hack" the WOZ OS, whatever OS and encryption is used? Absolutely. Will someone? Highly unlikely. For now.
I suppose someone could spend 10,000 hours trying to figure out how to exploit the WOZ OS. But what would be the point? To demonstrate how much idle time you have to spend on things that don't matter? The Iphone is jailbroken because there is money to be made in doing it. Plain and simple. Thousands of themes, add-ons and other programs are sold every year on Cydia and other places to the jailbroken community. There are millions upon millions of Iphones in circulation and so even if a fraction of them are jailbroken, the apps make money. And the hackers can pound their chest and make a name for themselves for hacking big bad Apple.
As for WOZ, while it might be a big deal here on Pinside, the rest of the world does not care about this game. There is zero demand for a "hacked" WOZ machine and so there is nothing to justify the amount of time it would take to hack it.
The only thing that changes any of this is if JJP remains in the market for say the next decade. As the number of machines increases, so too might the demand for a way to hack them. Until then, it ain't gonna happen.