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[Bigwilly]

1) I'd say no. He will take damage on his turn for starting in the cloud. Also the text about entering the cloud also implies to me that it is something that would only occur on the opponents turn - the opponent chooses to enter the cloud.
2) Again I would say no, but again he will take damage at the start of his turn. Otherwise it lets the wizard deal double damage. This is the sort of thing that always raises a red flag for me.