I don't want to comment on the moral side of Hackiulous, however I want to point out that jailbreak is always needed to to show Apple that people should be able to install whatever they want on their purchased and owned phone regardless of the type of applications.
Another good reason for jailbreaking is it shows Apple where there are holes in iOS. How many patches have been released, plugging up holes that jailbreaking discovered? Anyone remember the .tiff exploit for example?