Bum on view of innocence level
On the level view of Innocence( I think that's it, or this might be the level with his family.) Anyway, on the level with bum following you, your objective is to get to the other side of the graveyard with the bum alive. Throughout the level there are various gates placed by starkweather that will prevent you from going through them. To get through the gate all the hunters in the area must be killed, and the bum must be right behind you.
Only then will starkweather open the gate, and let you pass to the next area of the level.
Oh, and when you tell the bum to stay, watch and make sure he goes into the shadows, not near them like he usually does. He's nothing like the journalist on the level press coverage(who loves to walk into gunfire, and fall to the ground and start shaking like Ashley from Re4.) But he will go stand somewhere, and there will be a shadow right behind him. Then people will shoot him/stab him, and he'll stand there, drunk as ever.
If he does happen to stand near a shadow you can fix this problem for him. Either walk as far as possible into the shadow, and tell him to follow you, then tell him to stop when he's in the shadow. Or, run up against him, till cash manages to push the fool fully into the shadow, that way he'll be safe, and you won't get a game over.
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