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If there's something heavy you want in a town, it might be faster to do quests in that town for Influence and buy that town's type of Furniture tickets from the Secretary and use those to grab it.
You need to join the Thieves Guild in order for the trainer to have the option available to you, so talk to the person at the bar blocking the doorway to the stairs leading down to start the quest.
So if for example, you have 20 strength and just learned pick pocketing (so its level 1), then you would only be able to pickpocket items that weigh 3.2s or less. Anything heavier will just say "it's too heavy for you to pickpocket".