I don't really expect to win in a multiple opponents situation unless I have a weapon or if the guys are amateurs and just runs at me. Striking or grappling alone won't really make a difference. Personally, I think that striking combined with grappling is your best bet. Hit the first guy really hard somewhere (throat, eyes, groin?) and if you can't hit the second one, I guess do a takedown on him. But that's just me, and it might/might not work. It's just what I would do if in a real self-defense situation.
As for your master's encounter....it depends on the experience of both the fighters. It doesn't matter what art/style you practice, it really comes down to the individual man doing the art/style. Just use what you think is good against a grappler's attack. For me, sprawling is a "sound" strat I'd use. But I do agree with you about standing up, I'm more of a stand guy myself but I'm open to groundfighting if need be.
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