The quest should require two parties,
A caravan party, and a raiding party.
For example...
Every hour on the hour, between junktown and hub, there is a meet and greet between AI Carvan, and AI Raiders... you can make it a random spot, just so long as the encounter occurs.
You go to town, or a raider base, and can either Join the caravan, and win defending it against what will likely be AI... or you can join the Raiders, and pillage the convoy which will likely be AI as well.
But...
There's always the chance PLAYERS will be in either party. mixed in with AI NPC's etc, etc. in TURN BASED combat, so even damn blue suits have a "chance".