Some of the choices are strange, and they don't often go for the really star players. Kane, Toews, Stamkos have been on it recently, though.
Well, of course! But it's just my reasoning for fun, with a healthy bit of subjectivity.
As far as a simulation, it's as realistic as it's been. You can only compare to what has come before it when rating it, not against an imagined ideal.
Taking a lower league team to the top is definitely more challenging, and usually more fun.