@Eddie I will try to do my best to answer your questions, sorry for late response.
Do you think that he did anything wrong
It was unethical. I don't like sting operations.
or just that it doesn't perfectly fit the definition of the flag?
It does not. There was no contract.
Would you consider it untrustworthy behavior regardless of any technical flag language?
I can only say that I would not share any info with bob. I also think it is good that some accounts are exposed, especially that account with green trust.
Hm....can you understand this?