I suspect the worst software is the kind where the person buying it is not the person using it. This might also explain Apple's recent successes.
Are you saying that Apple is succeeding because their customers are their users?
Or are you claiming Apple software sucks, and every ipad sold was a gift?
Yes, and they have different priorities than the CTO or IT manager, who may select enterprise software by feature checklist (or other priorities) rather than end-user experience.