I can understand the Judge's points, although he might be stating them more absolutely than necessary.
It is very true that many guys are pursuing women who are out of their league. A thin women is NOT going to be initially attracted to a slightly overweight man. A woman with a sense of style is NOT going to be initially attracted to a slob or to a guy who shows that he has no sense of style. Notice I say initially attracted.
Game can always trump looks, but the problem is initial attraction. You can't even get into the game to begin with unless you show that you posess self respect.
I repeat: Self-respect in a man is what women are looking for.
That means she will accept your approach if you show externally that you have a sense of style, neatness and cleanliness. You do not have to be blessed with innate, natural good looks. If she sees that you have a sense of how you present yourself to the world, the looks barrier is largely mitigated and you can get your game on.
A nice hair style, stylish clothing, clean/polished shoes telegraph to her that you are a man who is in command of his life and who posesses self-respect. As an aside, let me tell you something... after your face the very first thing she will look at is your shoes. Bad shoes ROUTINELY kill chances with women. Women are shoe-obsessed, and nice clean shoes cover a multitude of sins.
For men, looks = overall shape, boobs, legs, ass, femininity, etc. For women, looks = Self-Respect, body language to a degree, and command over life. She is interested in one thing, when you distill it down. Power. A man who has command and power over his life, as evidenced by his bearing and "armour" (his clothing, for you slower ones), is invariably going to be very "sexy" to her. At the very least, she will be intrigued by such a man, in spite of his looks. "Intrigued" is the only green light we need to start spitting game.
A woman will only give herself over (and feel good about it) to a man who she perceives as more valuable than herself. Why allow her quick, initial filter take you out of the game before it even starts? If you're not good-looking, do the best with what you have and they WILL take notice. Show her that you're a force to be reckoned with. Show her that you respect yourself first, above all others.