Hardcore had a great post there. Sweeping untrained people who have little base on the ground is not that hard even if they're trying to hit you. It can get a little harder depending on the weight and size of the person but I pretty much agree completely with Hardcore's post.
As far as 2 on one..... well I actually had to use groundfighting in a self-defense situation against two people once. Lucky for me though that the one standing was focusing on trying to pull me off the other instead of kicking me in the head. But it was my grappling background that allowed me to fight and get back to my feet against even two people.
"Ryu:
When should you pound instead of fight for position and try to break? "
In my opinion the best time to ground and pound is when you have control of the person, and you can hit him uninterrupted. Ground and pound can become extremely tedious and not that damaging if you're constantly trying to fight for control, insert a punch here and there, etc. For a street fight I'd say you need to be able to hit uninterrupted. That's when the KO's happen.
Other than that, if the guy is good on the ground, I'd say to break away and get back to your feet. You're only gonna be able to do that with good grappling know how.
Ryu
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