The Bandit Challenges will focus on you being a bad guy, plain and simple. You will be robbing people, trains, amassing a hefty bounty, and even stealing wagons from people. Depending on how you do this, you might want to leave this set of challenges for last, especially if you focused on being a good person and increasing your Honor.
Bandit Challenge 1
The first challenge will have you robbing five townsfolk. This is cumulative and doesn't have to be done at once, so you can space it out over time. Remember that the people have to be inside of a town when you rob them, plus you will likely be seen doing this, so you'll earn a bit of a wanted level. To do this, just focus on a person with L2/LT, then press the Triangle/Y button to pick the rob option. You may need to hold them up at gunpoint or threaten them a little more to get them to hand over something.
Bandit Challenge 2
Your second challenge will require you to either rob a coach or return two stolen coaches to a fence which can be found at Emerald Station. You'll be able to simply rob any coach from travellers that are roaming about. If you dont fancy robbing the coaches and delivering them you can always rob the lockboxes on the back to complete this challenge instead.
Bandit Challenge 3
Your third challenge is a simple one, as all you'll need to do is rob a cash register in four different stores withing one ingame day. The best option is to head over to the general store, gunsmith and doctors in Valentine first, once you're there aim your weapon at the person behind the cash register and press the rob button. For the final store make a quick trip over to Strawberry and rob the final store to complete this step.
Bandit Challenge 4
Your forth challenge is similar to challenge two where you'll need to rob three coaches or deliver three coaches to a fence within once ingame day.
Bandit Challenge 5
The fifth challenge is an easy one, as all you'll need to do is stay within one area and commit as many crimes as you can until the wanted fee is at $250.
Bandit Challenge 6
Your next challenge will require you to make a little trip over to Clemens where you'll need to steal 5 horses and sell them at the fence nearby.
Bandit Challenge 7
Following the same path as the first challenge you'll need to rob some townsfolk until you rack up $50, simply head over to Saint Denis and keep a lookout for people that are well dressed as they may have a higher chance to give you more money.
Bandit Challenge 8
For this challenge you'll need to sell seven wagons at Emerald Ranch, this challenge is pretty simply as there are plenty of wagons that roam in and out of the ranch.
Bandit Challenge 9
This next challenge will require you to use your lasso and tie a person up and then take them over and place them down onto any tracks, repeat this three times to complete this challenge.
Bandit Challenge 10
The final challenge will require you to complete five train robberies without being caught or dieing, simply purchase a train ticket and get on the train and wait until you gain control of your character, then point your gun at a passanger and press the rob button.