1) Carson can use an action to give another investigator a free action. If he uses this in a monster's space does he first have to evade? And if the investigator that receives the free action is in a monster's space also, do they, in turn, have to evade?

2) Ashcan's dog, Duke, allows him to trade with any other space in range. Does this mean that he can trade with any and all other spaces in range at the same time, or can he only trade with one other target space in range? And if the latter is the case, does this occlude the space he is in, thereby treating it as if he is standing in the target space?

All questions aside, I gotta say I love this game!

1) You have to resolve an Evade check when performing an action that is not attacking the monster in your space. So, if Carson spends an Action to give another investigator an Action, he's not performing an attack. Thus, he has to roll Evade. If an investigator receives an extra action and wants to spend that action by performing an action that is not attacking the monster, he has to roll Evade. The source of your action doesn't matter, it's the type of action you're resolving that matters for checking Evade or not

2) I don't have the game with me, so I can't check the wording on Duke, sorry. Possibly someone else could help better here. In any case, the source space is always considered Range 0