Richard is not sure what Sean would want to do about the hideouts and encampments, but rather suspects Sean would like to do something, so he questions specifically about each one of them:
1. Name, type and purpose (camp in the woods, single building, hidden stash, whatever; (semi-)permanently occupied, occasionally visited, whatever).
2. The number of occupants and the type and the amount of traffic (army, slaves, cargo, vehicles).
3. The defenses (forces armaments, fortifications, installations).
4. Location (assuming this was already given to Richard, but I'd like to have it too, relative to the mutant lab).
5. Presence of radio equipment. Presence of bells. Presence of valuables and vehicles.
6. Which one of those was used to host the multitude of quick-response bikers and what are the other quick-response forces beyond that.

Then Richard asks about some other stuff:
7. How do they tackle the diseases of The Gutter?
8. How do they source weapons and transportations? If something is produced at the northern factory, can he explain the strange choice of weapons they produce? Like, Bergmann MP18 would be a very strange choice to produce nowadays. Or do they have a stock that lasted them 50+ years?
9. What can he say about Massachusetts as compared to Vermont? About Boston? About Springfield? What role has the army there, what activities it does there? Are there any other factions or unaffiliated groups or individuals?
10. The same questions about two states south of that.
11. What is the purpose of marking themselves with tattoos? Is it to prevent desertion or why else would not normal ID documents suffice?
12. Is there a way how we can learn who are their allies/agents inside Bread Basket? Meaning, they were smuggling chemicals out of the city, so there must have been some and maybe there still are?

Spoiler
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Did the prisoner say anything actionable about The Gutter? Like some places worth visiting or some routes from/to aboveground places worth visiting?

This should total 2 more hours of interrogation and we'll then proceed with the next steps.