The thing about jailbreaking is you have to keep doing it with each firmware update. Until they decide to let the homebrew community play without disturbance (pretty rare). And sure you can keep doing it after a firmware update. Heck on the Sony PSP they've created ways to upgrade and downgrade your firmware just to play those games that do firmware checks. It's just, are you really up to the task. At the end it just seems the same amount of work as learning whatever OS and the software that goes with it on another device to me.