Rob $50 worth of cash and valuables from townsfolk and travellers - Aim to hold up formal looking townsfolk as these hold the most valuables.Simplyy steal 5 horses from riders, barns or carriages and bring them to the horse fence. Steal 5 horses and sell them to the Horse Fence at Clemens Cove - The horse fence is located just north-west of Rhodes and will purchase any horse you bring him.You will amass a bounty of $250 fairly quickly by killing law enforcment. Amass $250 bounty in one state - I did this by hiding on the rooftops of Saint Denis and powering my way through the police that charge my way.
Rob any 3 coaches or return any 3 stolen coaches to the fence in a day - This is the same as Challenge 2, you just have to do it within a day. Rob the cash register in any 4 shops in one day - I think Saint Denis is a great location for this challenge because of the number of stores to choose from (Avoid the Gunsmith as he will return the favour by pointing a gun at you and potentially shoot you). You can find 2 coaches by riding around the surrounding area of the Fence. When travelling you must steal 2 coaches and return them to the Fence - you will also get some money for this challenge. Rob any 2 coaches or return any 2 stolen coaches to the Fence - The earliest Fence you can unlock is one at Emerald Station, east of Valentine. Hold up 5 townsfolk - This can be done by simply approaching some townsfolk, locking onto them by holding choosing the 'Rob' option, and successfully robbing them. 
Below are the required tasks: Bandit Challenges
So you must complete the first task to unlock the second, then the second to unlock the third and so on. Only after completing one tier the next task will unlock.
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