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I don't know if it is just a return to the comfortable world, at least in terms of motivation.
I believe Smith and can understand the idea of wanting to continue to work with characters you like. I think many good writers and filmmakers feel such a pull. The love of a character is not limited to only the audience after all.
Ray did his Apu triology as one example. John Ford did it to, at best slightly altering names or characters but basically revisiting the same situation and characters with his unofficial trilogy (plus others) including SWA Yellow Ribbon. Tarintino continues to fiddle with the idea of getting the Vega Brothers back on screen.
Many filmmakers like to revisit characters and find something new within them. They find them interesting subjects or the setting to be an interesting world to move characters around in.
Maybe Scoresese was just "playing it safe" when he did Casino, maybe Ford and Ray were doing the same. Leone and Eastwood...all about the safe, familiar work too. Heck, maybe that's what Hitchcock was doing when he remade his own Man Who Knew Too Much.
Not everything is a cash-in or an uninspired safety net in the world of revisiting topics in narrative art. Smith has already shown an ability to do films of different tone and theme within this same world, even if visually his films remain the same. Certain Clerks, Mallrats, Chasing Amy and Dogma are very different genres and topics that often don't have cross-appeal to fans of the other films.
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