Many of the moves we see BL perform in the movies were designed for show. He both realized and expounded upon their limitations in street combat. An example would be multiple spin kicks and lowering your guard simply for visual effect (though you could do so in an attack by drawing).
He really did kick the white guy for hitting him, I hear. The man laughed about it later, and they weren't exactly bitter enemies.
Yip Man taught him Wing Chun, but he learned various things from various folks. I don't think he every met Jack Dempsey (I could be wrong there), but he did glean some principles from him, such as the so-called "falling step." JKD is a series of such principles woven together and guided by the student's self-awareness and personal expression. Eventually, if you continue, you should find yourself breaking away from some of the things your Sifu teaches you. That is as it should be.
It is impossible to say who BL could or couldn't have beaten, really. He never competed because competition wasn't his purpose.
Don't give up on the right-lead yet. It gives the fighter some powerful options. You should work it hard until you sincerely believe you cannot progress in your proficiency with it, or it compromises your fighting skills over a long time. Absorb what is useful, reject what is not, add what is specifically your own. But before you reject anything you must be able to articulate why it doesn't work, and only do so after making an honest attempt at making it work.
The shin-knee kick is one of the more powerful techniques, when its proper execution is mastered. I don't see a problem with your first class, from what you said.
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A broken mace is still a weapon.
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