For the Pickpocketing part make sure you only take one item at a time, and Quicksave after each successful attempt. If you take everything the person has at the same time it only counts as one pocket, but if you back out, save and then go back in it'll count that as a new pocket picked. I got my 50 pockets with only three or four people, the best thing to do is fast travel to a town, wait till night and get them while they sleep.