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If you're not sure, if you can pickpocket someone or you know you barely can, go to Bosper and buy the ring of dexterity and belt and ring of skill from him. They will help you a lot with pickpocketing early on, trust me.
At some point you get quite a lot of experience from it. You also get a tidy sum of gold, which is always useful. You also need pickpocket to complete the "Joe" quest. There are also a few NPCs who carry an item instead of gold or a key, but those are far in between.
Only 1 blood chalice is in a chest you need a key for. And that person is Valentino. And you can just beat up Valentino. You do it when he goes back from Coragon's Tavern to his house between 4 and 5 o'clock in the morning. That way you also get a ring from Regis for beating up Valentino.
2. Learning pickpocketing is a useful skill and it is fun.
Every time you pickpocket something you get XP. The XP increases the more people you pickpocket from. Since there are several hundred named NPCs in the game which you can pickpocket it sums up to more then 25000 XP over time.
And if you do it right you won't even have to invest much in dex because most of the dex points come from power ups like stone tablets, praying, NPCs and so on.
Not only did you do the exact opposite of what OP requested, but you also forgot someone who has a key to a chest with a blood chalice who can't be beaten up and the only way to obtain his key is via pickpocket. But by all means, my advice is "bad" :)
You need pickpocketing to complete this quest, not for valentino. Check out the link d'amarr provided. You will see which one I mean. And the dude asks for no spoilers you just tell him everything.
This is wrong. There is one NPC that must be pickpocketed for a chest key.