After killing the 3 rival leaders, Jammer gave me the quest to assault my first settlement. Completed successfully, that quest works just fine. However, In It For the Money won't update and Jammer keeps telling me to go meet up with the assaulting raiders. I updated to the 4.0.0a Hotfix and that didn't fix it. I still have the kill Jared quest marker (even though he's dead) because I used console commands to get around that bug before the hotfix came out, so it's possible that now the quest is just broken in general for me. I have reloaded a few saves and tried playing vanilla quests for a bit, but that doesn't seem to help.