What are two questions you would ask Montresor from the story "The Cask of Amontillado"?

I suppose I would want to ask what so many people have asked about the incident: Can you give me some examples of the "thousand injuries" you suffered at the hands of Fortunato? And in line with this question I would also ask: Why did you continue to associate with Fortunato if he was injuring you so frequently? In lieu of being able to question Montresor directly, I have had to make my own guesses about the answers.

Taking the second question first, I have guessed that Montresor is dependent on Fortunato for a significant part of his income. Montresor is poor, Fortunato is rich. That is a strong clue that the poor man is receiving money from the rich man. Since they are both connoisseurs of fine things, I would guess that they both earn their livings by dealing in luxury goods of one kind or another. Montresor does not say that he is not a good judge of wine but only that he is not a good judge of Spanish sherry.

Venice is a decaying city, but it still imports expensive goods from the East. There are also many impecunious aristocrats who are living in decaying palazzi and selling off their possessions one by one in order to survive. Both Montresor and Fortunato, who know values and have connections, could provide a needed service by buying and selling such things as oil paintings, antique furniture, and "gemmary." But Montresor may often need Fortunato's help in these one-of-a-kind transactions. This would give Fortunato opportunities to take advantage of Montresor by demanding a larger share of the profits, by charging Montresor usurious interest, by cutting him out of deals he had been the first to discover, and by numerous other such "injuries." This would explain two things: (1) Why Montresor continues to associate with Fortunato, and (2) Why these "injuries" were not known to other people. If the injuries were widely known, then that would cause Montresor to come under suspicion when Fortunato turned up missing. But only the reader knows about the thousand injuries, and even the reader doesn't know what they were.

The first question, "Why do you continue to associate with Fortunato?" is already answered by the answer to the second question. Montresor has continued, not only to associate with him, but to pretend to be his best friend, because he is making money off the man and can't afford to alienate him. But something new has happened recently.

THE THOUSAND INJURIES of Fortunato I had borne as I best could, but when he ventured upon insult I vowed revenge.

Montresor will put up with the business injuries, but he will not put up with personal insults. I would not ask Montresor what that insult might have been, because I can only ask two questions and would prefer to ask why he has continued to associate with Fortunato and what are some of the injuries he has suffered. I would assume that Fortunato is becoming abusive just because he knows Fortunato will put up with the business injuries and knows that Montresor needs his loans, ad hoc partnerships, finder's fees, and other financial help in order to survive. Fortunato is sadistic. He "ventured upon insult" because he wanted to see just how much Montresor would take. If Montresor swallowed one insult he was sure to get insulted again. Montresor knows this, and this is why he "vowed revenge."