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Fallout: New Vegas Hints
Return to Milo at the NCR Checkpoint.
1 of 3: If there are still hostile Legion soldiers in the Nelson area, Milo may either go after them or stand on or near his hilltop and wait for them. If that's the case, you won't be able to talk to him right away.
2 of 3: See if you can wait an hour using the Wait feature while standing next to him. If so, you may be able to talk to him then. Otherwise, see if you can lure nearby Legion soldiers to Milo so he'll kill them for you.
3 of 3: When you can talk to Milo, tell him you put the captives out of their misery (or rescued them if you did that) to get some NCR fame, some Caesar's Legion infamy, and 50 bottle caps.