Maybe look at apps themselves? Instead of trying to lock down the phone itself, make it so apps cannot run on a Jailbroken phone.
There is technology to restrict which phones the apps will run on; but it has been cracked. I doubt if there is an uncrackable-method of app DRM (or at least, there isn't any which wouldn't also be a pain even for the legitimate buyer).
Apple could EASILY solve the masses of jail breaking by allowing the things must people are jail breaking for not related to piracy.
Those things are Multitasking, customizitino to the home screeen, allowing to install apps from places other than the App store. App store can be the "safe place" for users to get apps. In safe I mean they ahve been check out not to cause problems but this gives people the option to get apps straight from the Devs or apps apple rejects like GV.
That would be very nice, but unless Apple included every single feature that everyone wanted, some people would still jailbreak. I don't think many companies would let the customer base have complete control over the feature set like that. That might change in time, as we stop viewing platforms like the iPhone as a "phone" and more as a complex mobile computing platform.
It's funny how many posters in this forum did cheer SJ letter to music industry to remove DRM from music files, after all DRM was one of the music industry move to limit piracy. But crippling the music files has proved to be a failure while adding to the image of the music industry being greedy. So why so many posters are cheering Apple for keeping crippling the iPhone as a move to limit piracy? I guess now that it's about your pocket, and I believe that many posters here are app developers, sound different, doesn't it? While in no way I'm suggesting that piracy is OK, I see this as a major FAIL.
Instead, app developers, please concentrate on the quality of your apps and pressure Apple to create a way to allow trial of apps, and if your app is good you'll see sale increase. But what is going to happen to the other 95%?
As I mentioned in a previous post, music files and games are different, which is why music DRM failed so badly yet app DRM might not.
It's extremely difficult to make a DRM system for music that lets people play their music on their mp3 player, home sound system, car stereo, console, and media extender. People expect to be able to play their music anywhere on any device. Also, people will listen to their music for years after buying it, the DRM system has to still be supported for decades.
It's much easier to make a workable DRM system for apps (games in particular). Apps aren't portable anyway, no one expects iPhone apps to work on a PC, or PS3 games to work on a Mac. So the DRM system needs only be supported on one platform. In addition, games in particular tend only to be played for a short period, certainly not decades, so there's less need to have a DRM system which is supported for that long.