- Steal 500 gold in goods from Riften.
- Steal 500 gold in goods from Markarth.
- Steal 500 gold in goods from Whiterun.
- Steal 500 gold in goods from Windhelm.
- Steal 500 gold in goods from Solitude .
You may need to steal 500 gold worth of items from the respective hold's keep. It is more of a Robin Hood thing in which you steal from the rich, in this case the Jarl of the hold, and give to yourself.
Confirmed (PS3, Xbox) you do not need to steal from the city's Keep, anywhere around town will usually work. But not always. (ex. Riften)
- You must not be arrested during the quest, otherwise the quest will be failed.
- Being caught stealing an item will not count towards the total sum stolen, even if you are not arrested.
- If you are doing this job in the same town as one of Vex's jobs, her items count towards your total, meaning both jobs can be completed at the same time.
- If you steal an item, remove it from your inventory and then pick it back up it counts as a new theft towards the total. Therefore if you find one reasonably valuable item you can just steal it a few times rather than searching for other items.
- If you are sent to Solitude, go to Bryling's house. He has several valuable potions and is very rarely home, you can easily rack up 500 gold worth of stolen good in a matter of minutes.
- If you are sent to Solitude, the rightside room of the top floor of the Winking Skeever contains potions that make up the total and no one is around so this is another quick finish.