Question Jammer is depressed

[fonixfenix]

All the time I talk to him he says he needs time, to go see opheila or the raid board. Since then, I conquered all the settlements except the Castle and spectacle island. I take it he's broken? A broken man, a broken program.

 

[wanderer762]

This is where I'm at in my second playthrough.
Should I keep taking more settlements and hope that eventually the story will que up again? Should I quit and start a whole new game?