I haven't finished the game yet (though I have spoiled myself), what I can say in regards to that is that Dutch never cared about really making a better life- in RDR John tells him how "he always has a plan", to be it seems that what Ditch truly cared about, all he really wants is the life of the outlaw. The money never mattered.
Controversial, but I think Red Dead as a series is done. There's only so much you can do with its themes and message, even RDR2 feels like a wee stretch because of how the first game was about the end of the west anyways.
With how long Rockstar takes now to make games, I would be fine if RDR was laid to rest and they just rotated GTA and a new IP. Just look at how many games they released last gen, and take in that RDR2 is their first game this gen, and this gen is almost over so I doubt we will even see another game anytime soon.
I would be down for a RDR remake though, one that incorporates the story and references from RDR2.