Assist.
First, run a few of the ‘Main Story’ missions (with the yellow markers). These will usually net you a decent payday because you will probably have to kill a few folks along the way & loot their dead carcasses, to find valuables that you can either sell, or keep for yourself.
Especially run the main missions that involve the old guy named
Hosea. He usually has a decent ‘money making’ scheme (or two) up his sleeve. First, I think he takes you to hunting to find a Legendary Grizzly Bear. But his 2nd or 3rd mission (I forget which) will involve robbing a stagecoach from a pair of dimwitted farmers (father & son).
Hosea will cause a distraction to lure the 2 farmers out of their house, which gives you enough time to sneak around back & commit a burglary on their home. Search all the cabinets & drawers. Take everything you can find (both upstairs & downstairs) and keep an eye on their location (ie the 2 red dots on the map) so you can slide out the backdoor again before they get finally tired of Hosea’s gibberish & come back inside.
Then you & Hosea will both sneak into the barn nearby & steal their stagecoach... and deliver it to the Crooked Stable Owner (I dunno his name). This mission should get you a few hundred dollars of cash & burglary items, plus another few hundred dollars for selling the stagecoach.
SIDENOTE: if you have a large bounty on your head, the local shopkeepers may be hesitant to do business with you, so running this stagecoach mission with Hosea will unlock
‘The Fence’ in most cities, where you can now go to sell your stolen merchandise discreetly, even if you have a bounty on your head.
If you want to make even more money, run the
bounty hunter missions, or get
treasure maps from helping random strangers, in side missions. The bounties are posted in the Sheriff’s office in every city. Walk in, and talk to the Sheriff and he will put you to work. Most of them pay about $50-$100 bucks, or so (sometimes a lot more) & they are usually pretty easy to chase down / ‘capture alive’ with a rope.
Another way to make decent money is to talk to/help out the
WOMEN in the camp.

Do some of the 'chores' around the campsite (marked by the small black dots on the map) and/or take them into town if/when they ask you for a favor... and they will be your ‘eyes & ears’ in the city... and will inform you of ‘easy marks’, or the houses of lonely widows, or small heists, or rival gangs and ‘illegal business’ (or poker games) that you can rob (or burglarize) to make a quick buck.
At first, the jobs they tell you about will be small... but the paydays should get bigger & bigger the more you engage with them.
Running the main story missions will lead to big heist missions every so often, but the ‘biggest paydays’ are not that common.
Lastly, if you want to make about
$9,000 REALLY FAST, watch this hilarious video below...


