Hi there! Thank you for your questions and your interest in the game.

If he has the box in his hand when he 'falls through', he will definitely carry the box over with him into Chicago. Anything a person has on them or in their hand will come along with them when they end up in Chicago.

You could always give him an elemental power of some kind. Maybe the whip itself, he could have the power to add fire or electricity to it which would cause extra damage. You could also turn him into a shapeshifter and pick a large, offensive animals for one of his forms. There are unlimited options really to work with even when considering giving him something offensive. You could make him stronger when he hasn't transformed into the warrior for instance too. The Rift can also take things away from people or change small things about them. It's not always an ability, but that would be up to you as to what you want to do with him.

I hope this helps and if you have ideas for rift changes and want to ask if they sound acceptable, feel free to ask about them here.