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For the challenge it's easy:
Buy ticket from Emerald to Valentine - ride - run back to caboose and steal Canned Peas.
Buy ticket from Valentine to Emerald - ride - run back to caboose and steal Canned Peas.
Repeat until the challenge completes. You may see a guy near the back, if you run out of Canned Peas and have to go for the Palmade. Just run away and don't shoot him - he won't follow you.
For Fun/Profit?
There are much more lucrative ways to make a dollar than robbing trains. <---it won't be as much fun, but you'll be rich.
Things will get dramatic.
If you don't want a lot of Drama - steal some peas.
The Challenge says:
Rob 5 Trains and getaway clean.
Pretty easy to get away clean when you steal peas and nobody sees you.
Pick one and go with it. You can have as much, or as little Drama as you want.
If you want to get rich - start selling Steelhead/Sockeye in St. Denis at $5.35 each.
Brew and sell Potent Tonics with plants you pick - 100% profit - plants are free.
Nobody will shoot at you and you won't rack up a large Bounty.
Hunting is fun, but you won't get rich - fat maybe, but not rich.
Where is my question.
Van Horn?
Those guys won't be robbed easily, in fact, it's real easy to get the whole town shooting at ya.
St. Denis is better - the guys in the top hats probably don't have a gun, but if they do it's in their Wife's Purse along with their doo-dads. Unfortunately, while the targets have the most cash and valuables - they're protected by the most police.
You will probably generate some Drama.
Make sure to hit the 'Rob' button and don't just aim your weapon at them. You want to make your intentions clear and that may enhance the outcome - I don't know really.
I find it pretty rare for people on the roads between towns to even give the option to rob, let alone having the option and them refusing and attacking. I even had a milkman pull a knife on me after I lassoed him off his wagon. So it has always been rare for me.
I think the chances there might also be related to your reputation, whether your honour is low and whether you have a bounty etc, people being less likely to let you rob them if they are scared in that way, and rather try to just fight back.
Certain NPCs almost always let you rob them however, usually the ones that have no guns, like Juice said for example, the fancy pants in Saint Denis are easy targets so long as you can get them away from witnesses.
Then I surrender and go to jail - 5 times - a little vacation and I get more honor when I'm done than when I started...lol
You can rob passenger trains for quite a bit of cash and loot if you can manage to rob all the passengers and open the vaults with dynamite. I would estimate each passenger train carrying something between 250-600 bucks worth of cash and goods. There are some variations in trains though, not all are passenger trains.
You can mess with strangers and get them to either run away from you or try to follow and fight you into areas and get away with it, it doesn't work all the time, sometimes it will cause others to attack you or get the law on you, but it can be a bit of a minigame in and of itself to try.
Edit; I know that isn't your style, but it is possible nonetheless.