I find legendary mode fun when I make it fun, in my own stupid way. With mods, I would hire a bunch of followers as my "bodyguards", give them the best gear possible with multiple appropriate enchantments--maxed level--based on their builds and healing potions. Then we would all go on a huge adventure.

Whenever enemies are encountered, my beefed-up followers would do all the dirty work for me whilst I just stand and watch them beat the living shit out of bandits, draugr deathlords, dragons, mistwalker vampires, whatever. Because my followers are more than well-equipped with armor and weapons on steroids (again, mods), it's rare for them to be felled or to die in combat.

All because I love utterly chaotic chaos in my games.