User blog comment:Jimeee/Skyrim 1.9 beta update adds Legendary difficulty and raises level cap (Updated Apr 8th)/@comment-6320696-20130330222015/@comment-67.177.107.19-20130331045736

You can do it infinitely. Kind of feels weird having when while using SkyRe, because it feels so useless. There is no way I would use the "Legendary" system when I can get my skills up to 300 and get all kinds of cool perks instead.