So much wrong in that opening set up. So much wrong with the entire video overall.
Also he has another vid where he shows how to snap someone's neck in guard, but says not to do it because it's dangerous. One of his students says "but what if we want to?"
I come from a practical fighting system so for us if it sounds too complicated then it probably doesn't work. The biggest problem is that these techniques are done while the "grappler" isn't struggling. Struggling changes the entire playing field and the opportunity for a possible trap could close in less than a second. All of those "opportunities" that he's speaking of for an attack aren't going to exist. At any point during that struggle on the ground, there may be only 2 or 3 opportunities to strike, with each strike having it's own risks. Imagine trying to do those traps with movement at this level of intensity.
By the way punching someone in the stomach while they are in a crunch position is going to be useless because the stomach muscles are flexed and your striking power is limited. That's why it takes multiple punches from ground and pound to have an effect. The punching just isn't going to have the same strength or power as it would if the person is standing up punching. Those wing chun punches look cool in the demo but in a real fight much of that stuff wouldn't be practical. The best thing a wing chun practitioner can do in that position is to put his effort into escaping from the grappler's strength. Wing chun is not a grappling art so no wing chun practitioner should not be trying to out grapple a grappler.