There are occasionally events when resting, aren't there?
And there were also days where there was no event, if memory serves.
Could you maybe replace the "no event" with pool of characters, still including "no event", where each character would get, say, 3-5 small conversations, some as short as 1 line without return?
Alternatively, the same with an option in the bar to just pass a little bit of time?
That would just include a char portrait popping up and a little bit of text, and some of those could be repeatable.
Admittedly a little bit more work, if you set a few flags for noteworthy events, like coming back from a mission with all but 1 character passed out, or having added a new girl or succeeded at a side quest, a character could mention that, clearing the flag, which would also happen after a regular rest.
In my experience, in a (partial) sandbox game where players can just with characters at specific times, in specific places, even just two different dialogues that completely repeat would give those npcs a feeling of, uhm, existence.
And I think that, once the story continues, there will occasionally be new dialogue options for the main characters, which are, by definition, new, then those small (to the player completely optional) engagements would be enough to carry until then. After all, while the point is to hide that fact best as possible, most players
are aware that this is a game.
However, this
is polishing, so please don't feel pressured to focus on this over the story you want to tell and probably find more motivating to work on.
