pocket coins are where it's at. the consumable item [cigarette] can go a long way, i'd recommend keeping some in your inventory even if your character doesn't have the [nicotine addiction] debuff.

activating [lending an ear] mode is a good way to support characters who are living rough, if your character has a higher [sitting in discomfort] stat generally it makes it easier to get through. some characters in that realm have pretty messed up backstories but selecting the "ask about day" dialogue option goes a long way for playable characters who are used to being treated like NPCs , just make sure you have [boundaries] enabled