Successful men do not want their relationships to be a challenge.

That's simply untrue. The most successful people are those who thrive upon challenge.

For a number of years I was casually dating someone that I found both extremely attractive (solid 11/10) and personally very interesting. The deal breaker for me was that she would make excuses for every bad habit that I had, trying to make life as easy as absolutely possible for me. I need someone who will encourage my best qualities, and discourage my worst, so that our relationship can help me grow to become a better person. I need someone who can challenge me.

It's perfectly fine if that's not the kind of person you're interested in, there are vastly more women around who won't challenge you. Don't go around insisting that someone must want to date people like you in order to be a good person though.