What makes the experience more fun when you jailbreak it? Just curious, since I've never felt any need to jailbreak my iPad.
Using hardware-accelerated movie players, drag-and-drop file importation via iFunbox, using your device as a hotspot (if you have LTE iPad or if you jailbreak your iphone), Winterboard themes, Gridlock (ability to put your icons literally anywhere and in whatever arrangement you want), Springtomize (ability to customize your status bar, dock, customize or hide icon labels, resize icons, change folders, change grid size of homescreen, and many more features), No Status (hide status bar in homescreen), tons of lockscreen customizations, add more functionality to Siri, etc..... And this is just what I use, and I use a lot less tweaks than most people.
So many more features than what you get on a stock iPad. In comparison, a stock iPad or iPhone experience is boring, in my opinion.