You're normalizing corruption here. Specifically, recommending bribery. That can land you in more hot water than whatever "gray-area" business you're running.
Not if you make sure all of the bribes are legal, or else lobbying wouldn't be an entire industry.
edit: In Illinois, at least, for it to be bribery there needs to be proof of an explicit quid quo pro e.g. a recording of you saying "If you give me X, I will do Y."
Note that "I'm going to give you X," "What a coincidence, I'm going to do Y" does not count.
