I think one of the main reasons he said yes to making Titanic was the possibility to have the power about his career. I mean of course he couldn't know how big it would be in the end (Leo mania etc pe pe) but Leo never was stupid. He knew he needed some huge blockbuster success to have the control about his future - well at least partially.
But he never went the easy way, I agree with that. It always seems so easy for him, but I think most of his movies are big financial risks, no matter what some people say, he would never take any risks with his choices of roles and movies.