The Jagged Crown can be kept by reverse-pickpocketing it to either Hadvar or Ralof after the crown is collected but before the quest is completed. Although the chance of success will show as zero percent, it is possible, but may require several attempts. The faction sided with at Helgen must be joined for the exploit to function properly. Once the quest is complete, the crown can be pickpocketed back from Hadvar or Ralof during one of the missions to retake one of the various forts involved in the Civil War, or, after the Civil War, in Riverwood. Using means of paralysis (such as The Serpent Stone), or boosted Pickpocketing improves the chances of recovering it successfully.
Or with console commands on PC: player.additem 000DA750 1
I have yet to begin the Civil War quests. If I desire to obtain this item, can I determine who I followed in the beginning of the game by checking whose house I am allowed to enter and sleep in? I am guessing that I can determine this by looking at which key I have in my inventory.
Get the crown from the Draugr (Jagged Crown quest)
Secretly put Jagged Crown to Hadvar or Ralof by reverse-pickpocketing... But remember that even if you have high level pickpocketing skill, it's still a bit hard to do this... So use item/spell that can paralyze him, or turn him into ice using Ice Form shout, then crouch... The first few seconds you won't be able to pickpocket, so repeatedly press the pickpocket button to make sure that before he stands up, you get to his inventory...
Go to Solitude and "deliver" the Jagged Crown (which is not in your inventory right now), quest complete...
Go to Riverwood Inn, and Hadvar/Ralof should be inside, now take your precious Jagged Crown and keep it... Tho like before, even if you have high pickpocket skill level, it's still a bit hard to take the item from him... So use paralysis item/spell or freeze him using Ice Form shout, crouch, then pickpocket.
I left Helgen with Ralof but joined the Imperial Legion. I tried to reverse pick-pocke the crown onto him while he was in Riverwood, but I either got busted (where I used Voice of the Emperor to calm him and to try again), and/or it told me "this is a Quest Item".
I've now restarted my game so that I could leave with Hadvar and I'll try and do this again with Hadvar. Really hoping I can get this work, as this is my favourite piece of headgear and I don't want to give it up, but I want to progress in the story.
Does anyone know if this will still work if I'm low level and have a crappy pick-pocket skill?
you can always just paralyze, freeze (or maybe ragdoll using unreleting force, im not sure) the target you are intending to pickpocket, then im pretty sure you will get a 100% succes rate