ios-deploy

No jailbreaking necessary. Edit: Can't reply further, but the way of doing this is much the same as installing unsigned apps on an xbox. Using a (free) developer account you can sideload things quite easy using something like https://github.com/ios-control/ios-deploy

Apple does allow developer users to install IPA files outside of the App Store. I can easily take an app off Github, build it with Xcode, and install it on my iPhone, for example. There are even scripts to do this similar to a "configure; make; make install", eg: https://github.com/phonegap/ios-deploy This doesn't require the $99 it used to either, anyone can do it, though it does require you to get a free signed developer certificate from Apple which signs the app (you'll also need to tell your device to trust your cert). You can even distribute an IPA file and install it via iTunes and not the App Store, but it needs to be signed by a trusted authority (your company; your dev cert; or most likely Apple, as long as it is a non-revoked cert).

Getting the code building with M-x compile should be fairly straightforward. For deployment + debugging, you could try this: https://github.com/phonegap/ios-deploy Looks like it runs lldb itself, but perhaps with a bit of work you could get it to interact with gud-mode?