I have just found what I think is probably the easiest way. For the 50 Locks just play through normally. Grind your way through all of the dungeons and you'll have this in no time. As in Oblivion, there are many locks in the game.
Now for the pick pockets, find a guard and place 1 gold in his inventory; repeat untill you have 50+ pickpockets. Took me literally 2 and a half minutes to get 50 pickpockets
- Always open jail cells and chests you find around Skyrim, even if you don’t necessarily want anything from in there.
- Always carry enough lock-picks. Buy whenever possible. Even breaking them earns you experience for that skill, thus making it easier to lock pick.
- Doing the Thieves Guild’s final mission, “Darkness Returns,” you’ll be able to get a special ability that will help you remain incognito. No spoilers!
Use the standing stone, the Shadow Stone and once a day players can become invisible for an extended period. That helps with pickpocketing. You’ll find it south of Riften, in the small mountain in the middle before the big mountain range to the south.
- You have to be crouched to pickpocket, and do so from the shadows and only grab when the reticule’s eye is closed (i.e. a thin horizontal line).
- Remember, it’s free to look, but grab something and get caught and they’ll turn on you and you’ll get a bounty. Always note the percentage… 90% ones are fairly risk free