"But what happens when one of the parties doesn't play Chi Sau properly, like the big red headed kid? What would that look like?"
Mike, I don't think that I gave you the answer to what you really meant. What I think you are saying is that what happens if folks won't play your game, in this instance give you the fight that you want. This is something that a lot of chunners don't see
..which is why I don't practice WC anymore BTW .
If you look behind the mystic, what do you have? You have a system that fights very close in using striking techniques, to assist this they use a training exercise called "Sticking hands" that is really the essence of the system ( Gary Lam makes this point over and over again, it's the chi sao that makes the system).and other stuff such as the wooden dummy and a couple of forms tagged on the end, and they fight face on..............so how can you beat them
easy just don't let them get close.Exploit their stance by going side on and use jabs rather than a barrage of punches like they do, use long range kicks or get in very close and wrestle them.
This is the story of all martial arts, somebody notices a weakness, develops a habit of doing something that exploits that weakness, i.e close in fighting in this instance.somebody else finds out what they are doing and develops counters to it and the system becomes redundant.
I believe that this is the reason a lot of old masters in China kept their arts secret...If you have never seen a Good chunner fight then it can be a real shock to the senses having to face one.but the same applies to any style if you hadn't seen TKD and had to fight one of them it would be equally difficult