It depends on how we define success, as others have pointed out. Anything can be used as a mask (or makeup, whatever analogy you want to use). Success, beauty, money, academic status, life experience, preferences, etc. It all comes down to a pride issue. If any of these things define a man, then I would have a problem with it. If they don't, he can be whatever he wants as long as his identity is rooted in Christ first and foremost. Rich, poor, middle class. Those are all of no real value.
As for personal preference, of course I would want someone successful. I want to be successful myself! Why wouldn't I?
But that's not what I'm looking for primarily.