Hipster doesn't leak as much information, but it is almost just as persistent. You can uncheck the "Contacts" button when you enter that preference, but only after the app sends your data. Also, if you come back to the screen, it reverts to checked. They are really filter buttons, and not stateful, apparently.
But yes, it doesn't happen every time.
Jailbreaking means so many different things to different people. I know it causes issues with Apple-sanctioned updates, but sometimes those issues are just plain worth it.
All the stability issues, all the battery life issues, and all of the downsides apart from a more complicated update process are first and foremost effectively made-up. There's no solid data to back those things.
Jailbreaking has time and time again patched vulnerabilities that Apple didn't (in a timely manner), and proven that it is a valuable part of the ecosystem.