Ironfist,
The progression in Chi Sao is parallel to the progression through the system - we start out stationary, like Siu Nim Tao, and progress as we experiment with different movements, like Chum Kiu and Bil Je, noting that the progression builds off of the previous experiences. When two people engage in Chi Sao, there are two egos involved so the urge to see who is “better” is present. One must focus on what you are training. The most difficult, but most beneficial way to train is to be cooperative and slow things down so you can “see” what is going on and discuss it. However, this must be looked at as a phase of short duration for different concepts. Can you practice one movement consistently, and that’s all you do for about a month straight? Once you have all the ideas and physical movements understood during that period, let it go and move on.
Chi Sao begins at Don Chi Sao. There is a lot to study there. Then move on to Luk Sao (rolling hands - understanding position), Jip Sao (catching hands - learning to maintain position when nothing is there), jao sao (running hands) and then Toi Mah (push horse - movement while rolling and maintaining the horse). One should “graduate” to Chi Sao when you have some sense of understanding these phases.
Chi Sao is an exercise that is not meant to be used for fighting. However, aside from being a “laboratory”, Chi Sao is a method of testing your skills. It is often recommended that you have a phase of having equal or senior level students “feed you the hands” first, so you can learn some basic movements such as lop sao, poi jong, and tan dar (trapping type movements). Then, for a more realistic feel use the Sidai (who can just roll) for you to honestly evaluate ideas. The final goal would be to play a higher level person with some confidence in your own ability.
A student should at the very least have some control over protecting their centerline with solid positioning before starting to hit. However, you should have a phase of training where you “let the hands go” checking distance to your partner and studying the consequences. This is where you can study martial attributes such as timing and relaxation.
Finally, you should think of your strikes as being supported by your body, not just “hits”. This is supported by what we call “phon sao”, or followup technique.
From the Kun Kuit - “Hit when you can; Do not hit when you can’t”.
Good luck in your Kung Fu