@fossball: I think we are going to need a roll to see how he reacts to your
questions.
I don't see anything in there to suggest a different Stat to CHA, so roll 2d6+1 (not that it makes much difference to you with all those +1s, but the Stat used is based on the fiction and affects the types of outcomes we can expect).
In this case I would think:
On a
6-: Something you said offends him and you have an incident, but you can still obliquely learn something from that reaction. The conversation is probably terminated.
On a
7-9: Something you said makes him (or someone else here) irritated and you have to calm things before you can ask more, but you can still obliquely learn something from that reaction, and can learn more if the conversation continues.
On a
10+: He sees that you meant no offence and answers your questions. You learn something from the conversation so far and can continue drinking and talking with this group if you want.
On a
12+: Something you said triggers him and he goes into detail about related problems in the area, you will learn a fair bit, and can continue to drink and talk with them, and possibly gain an ally.