He'll never be a legend because he's never dropped an album that changed the game, nor has ever been part of a movement that history will remember. To be fair, although I haven't heard the latest album, he has consistently put out above average music. I'm still waiting on him to drop something nuclear but I don't think he has it him. I like Ross and his persona doesn't bother me as Hip Hop has a long history of outlandish personalities and colorful characters. He stays in character a bit longer than most, and I think it's a combination of trolling and a possible mental disorder, but it is entertaining. Which is what we want, right? Are you not entertained?
Edit post: his ear for production is exemplary.