Upgrade 2: 1st Recon Survival Armor or 1st Recon Assault Armor when you complete the 2nd Quest from Boone. You will get this upon completing the 1st Quest with Boone.
Upgrade 1: 1st Recon Beret that gives you +1 Perception and +5% Critical Chance. Perk: Spotter automatically marks hostile targets in the area, this can help at night in case you do not spot an enemy or to differentiate between a friend or an enemy. You will need to complete the side quest “One For My Baby” that he gives you by talking to him in order for you to be able to recruit him to follow you. You can find him inside of the dino’s mouth guarding the town of Novac after 9PM. Info and Quests: He is very easy to get recruit from the beginning to and he offers a lot of help to you, especially if you have gone ahead and decided to play Hardcore mode. But he does not have to be the first nor may he be the first.
Location: Craig Boone is one of the first companions you should come across near the start of the game.