No he uses Outwit once, but can use it to outwit every opposing figure's power in either the Speed, Attack, or Defense slots. Meaning he can Charge, Running Shot, and Hypersonic Speed (or any speed power) on your opponent's theme team if they all share the same generic keyword with this power.

Does SP outwit automatically affect all generic keyworded characters on your opponent's force or would they need to be within 9 range as per his trait?

It would affect every figure on your opponent's force, if it was just in range, it would have said something to the effect of "each opposing character within range", but it doesn't

#211 still needs to meet the criteria in order to use Outwit. Normally, Outwit requires Line of Fire and Range, but the Trait allows #211 to use Outwit without having Line of Fire. Range, however, is still a limiting factor.

...but only on the target of the Outwit. It still affects the rest of the qualifying characters regardless of range or lof.

I just wanted to clear up any confusion around that.

Actually Monkey joe is right as there is no wording of instead...in the power...so yes it will have a normal outwit and an additional effect to counter powers in a slot...

"Great, kid; don't get cocky!"

An elegant solution to countering Improved Targeting on characters hiding behind a wall (IIM001 Iron Man, Bill Agent of A.I.M., etc.).

Could this models outwit trait stack with omega drive?

Yes, because Omega Drive modifies the use of Outwit rather than being a separate use of it.