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Going through the trouble to befriend him grants you a new Gesture, but you wont be able to buy his armor until you beat him. Pick you're route.

It's terribly easy to go by enemies in this game until you get to the lower chalice dungeon spiders/hell hounds. So don't be afraid to just run by some of them if you looted the place already. Old Yarnam has two shortcuts, find them and you can evade the Old Hunter's aim quite easily.

About the Old hunter: His AI like many of the enemies in this game have a range. Sometime bosses are easy and sometimes they bring their A game. He has never fallen off the top by himself for everytime I've fought him--Seriously! He has fought me tooth and nail for every time I approach him from entrance to Old Yarnam.

When I was low level and new to the game, he would actually drive me to the edge and push me off quite often. Probably because of my skill level, and so the only way I found to be able to kill him was to come around the shortcuts so he didn't see me. It would usually give me 1-2 seconds head start and if you rush to him, you can push him off. Otherwise, as soon as I neared the top of the ladder, he was already heading toward the middle of the platform. Good Luck.