Here's my suggestion. If you have a disneyland prison but you find a large population of the prison choose to break out of their cells each night, not to leave permanently, but just to do a few things outside the prison walls that can't be done inside the disneyland prison... I say the solution is... Create another wall outside.
Things like Backgrounder, Infinidock, Infinifolder, Activator, SBSettings, OpenNotifier, Parallax... Take the ipad, and in the settings menu, have a toplevel switch like you see on many PCs. Basic and Advanced Settings. Switch to Advanced, and then you can change fonts, colors, advanced multitasking features,etc... Take the top 20 Cydia apps and develop official Apple versions of them and incorporate into the Advanced Settings menu. This way, the simpletons can be happy as well as the techies...
If I had these things I might not feel swayed to jailbreak.
And people who don't like this idea, stay in Basic mode. I'm not taking anything away from your experience and you don't have to rally against the other side's desire for customization.
Everyone wins, including Apple for recognizing that we are individual humans, that the desire to individualize cannot be conditioned out of us, and then we can all have the iPad experience we're looking for.