Legendary difficulty came out allowing me to be challenged again with my level 65 character. I've finished the factions I wanted, beat the main quest, did the DLC's, and have explored nearly everything. Essentially I'm done but I want some more things to do. Radiant quests are sending me to places I've cleared before so that's out. Sure, I'll go do some unmarked side quests in Soul Cairn or something but do you have any ideas on what I could do to get a couple more decent hours out of Skyrim and this new fangled difficulty setting?

sounds like you need to start a new character

or just kill everyone..... either die a hero, or live long enough to become a villain right?

...I find that at least HALF of my time is spent organizing items.

same here

to the OP: if youre not roleplaying with your char, make a new one, and try to do so... will add a ton of things to do, and will lengthen the gameplay a lot... being a jack-of-all-trades that always does everything asap usually ends up pretty fast and is rather boring

I roleplayed my character as a vigilante Dunmer stealth mage and rarely fast traveled.

If you're getting bored, then it sounds like it's time to make a new character.

Try something you haven't.

well you can either try starting a new "adventure" with your char, or start off fresh, with a new char, with a new story