These challenges must be done in order, progress made before they are activated does not count.
Challenge 1 - Hold up five townsfolk.
Unlocks Bandit Bandolier
Challenge 2 - Rob two coaches along the road or complete any two coach robbery missions.
Rewards 25 Dead Eye XP and $5
Challenge 3 - Rob the cash register in any four shops in one day.
Unlocks Bandit Holster
Challenge 4 - Rob three coaches in a day.
Rewards 50 Dead Eye XP and $10
Challenge 5 - Amass a $250 bounty in one State.
Rewards 50 Dead Eye XP and $10
Challenge 6 - Steal five horses and sell them to the horse fence at Clemens Cove.
Rewards 100 Dead XP and $15
Challenge 7 - Rob $50 worth of cash and valuables from townfolk and travelers.
Unlocks Bandit Off-Hand Holster
Challenge 8 - Steal seven wagons and sell them to the fence at Emerald Ranch
Rewards 100 Dead Eye XP and $15
Challenge 9 - Hogtie someone and leave them on the railroad three times.
Rewards 150 Dead Eye XP and $20
Challenge 10 - Complete five train robberies without dying or being caught.
Unlocks Bandit Gun Belt