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Don't even need to jailbreak, nowadays you can build/sideload using a free iOS developer account, especially if the projects in question are open source.

You’d need a jailbreak to get the ability to JIT properly.

...which only works for a few days until you need to build/sideload again on a free account. (Or a full year if you have a 100$ a year paid dev account).

Sideloading isn't a solution because Apple artificially crippled it to make it only useful for demoing and testing apps, not as a secondary install method.

What's the latest iOS version that can be jail broken? With all of the exploits on iOS, I'd be pretty nervous running an old iOS version.

Isn't it a requirement that the iOS be exploitable so that it can be jailbroken?

Is your hope that the exploit for the jailbreak is the one and only flaw? :)

True. I guess my point was that, given the insane number of zero-click iMessage exploits there have been, you’d have to really not care about any of your data to use a jail broken phone.

Do you think this would work considering for all of the iPhone only WebKit has been allowed?