Depends on how you want to do a playthrough. Sometimes I would never sleep and just drink the night away. Sometimes I never capture bounties alive. Just really depended on what you were doing. It's why I appreciated RDR because it had some light RP elements.
Overall, money is just incredibly easy to get in the game. I was merely trying to think of other ways to get it in larger amounts.
The most fun way I think is robbing banks at night. Easiest one to hit is Armadillo. Use the bandana.
My favorite gun in the whole gun. Not very wield-friendly in real life, and it's a shame you couldn't use the 16 guage single shot barrel located underneath. Even more of a pain in real life if you had one of the models that didn't use a standard .36 or .44 calibur round.