I would like to know how native English speakers regard the opinion of authors of negative questions. For this reason I added the sentence "You're right." to each of the following examples (the examples are mine).
(1) Won't John go to work?
(1a) You're right. He will. — We think the questioner thinks John probably will go to work
(1b) You're right. He will not. — We think the questioner thinks John probably won't go to work
(2) Doesn't Bob wear glasses?
(2a) You're right. He does. — We think the questioner thinks Bob probably wears glasses
(2b) You're right. He does not. — We think the questioner thinks Bob probably doesn't wear glasses
(3) Didn't Fred do his homework?
(3a) You're right. He did. — We think the questioner thinks Fred probably did his homework
(3b) You're right. He did not. — We think the questioner thinks Fred probably didn't do his homework
Are all correct variants only "a" or only "b" or in every item the answer can be both "a" and "b" depending on the context?
Will your answer change if we make the questions more formal by separating "not" from the auxiliary verbs?:
Will John not go to work?
Does Bob not wear glasses?
Did Fred not do his homework?
Also, if we rewrite some one of the examples as tag question, will "a" or "b" be correct (or maybe both depending on the context)?:
(4) Bob doesn't wear glasses, does he?
(4a) You're right. He does. — We think the questioner thinks Bob probably wears glasses
(4b) You're right. He does not. — We think the questioner thinks Bob probably doesn't wear glasses