Superman Enemy
When two friendly characters that can use the
Superman Enemy team ability are adjacent to each other, the character
with the higher point value may be given a free action to immediately use
Outwit. That character can use Outwit until the beginning of your next
turn, if it cannot use Outwit already and continues to use this ability. If the
two characters have the same point value, their controller chooses which is
treated as the higher point character this turn.


Reading this I can't find anything that says it cannot be used more than once a turn, as long as the free action isnt given to the same unit. Can I do this with three 100-point units standing side by side:

Unit A uses free action with unit B and since they are the same points I give outwit to unit A. Now unit B uses a free action with unit C and I give outwit to unit B. Now unit C uses a free action with unit B and I give outwit to the only legal one left, unit C.

Yes. That is legal.

Player's Guide section 05 page 3:

^^ This is correct if they're in a triangle rather than in a line. If C is adjacent only to B, then he's been paired with B and given B the Outwit. He can't then be part of a second pair with the same character. If C were adjacent to both A and B he could form a pair with A and get his own Outwit.

Actually I'm having a hard time finding any evidence that you cannot do this. Lets pretend I have Wolverine, Agent of Hydra and Shang-Chi at 90 points each and they both magically gained the Superman Enemy TA.

I use the TA, determine that wolverine will use the free action and gain outwit. Then I use the TA again (because there is no restriction on using the TA itself) and give the free action to Shang-chi to use outwit.

True. True.

Player's guide section 01 page 2:

You might want to read the description of the TA again, especially the last sentence.

If you have chosen Wolverine to be treated as the higher pointed character, you can no longer choose for Shang-Chi to be treated as the higher pointed character on the same turn.