For my pull test? I leave the chocks in place.
As to the brakes, I'm sure others will chime in with better mechanical descriptions and terminology, but in short, most trailer brakes rely on an electromagnetic system with the magnet "sticking" to the drum, with forward motion, the magnet shifts and displaces the brake shoes. So yes, it takes some forward motion, the more poorly adjusted the brakes, the more motion necessary to engage the brake shoes against the drum.
Electric over hydraulic on the other hand, use more immediate hydraulic pressure to engage the brakes.
Hope it helps!