Sifu John Lobb is the real deal. You can tell by the way he fights and also by the way he explains - it's clearly coming from a place of deep understanding - he's trying very hard to get *you* to understand him, too...! Thank you for sharing your experience with us...!
Sometimes it can be good to pressure test with force. Chi sao without direction beacomes very tame and you cant really capitalize on anything. Its like two wrestlers where noone attacks. In wing chun you should always have forward pressure, its an idiom of the system. You can also get a workout in if you roll heavy.