Probably bad memory, but think, at least for several past versions, I never failed a conversation check (enemies always distracted etc.). Mentioning just in case of any bugs.
I would expect even non-combat encounters have strategical influence. Not like necessary part of campaign, but when you get it instead of a regular district combat, naturally compares to that. And one of the important combat outcomes is possibility to get intel. Additionally, has impact on district, thus consequently on gang (lowering income, # of troops). Etc.
Based on some things said, eg. if specific party members are present, think I initially thought it will lower crime in the area. Even can imagine if we have some reputation already, just a mere presence of Sam and pals would suffice for criminals to decide keeping their heads low for a while...
Cash or a gun, getting rewards... Thinking about this specific scenario - calming old lady and fixing her door - how do you, guys, feel about helping her out and getting paid for that? How that compares to her calling a regular repairman to do the job? It is a honest question, would like to understand how others see it. A quite common in games.
Not that I have any illusions about altruistic-looking things being altruistic, doing favors is known to pay itself eventually after all. Only that if it happens it's usually a bit later, more subtle, or in unexpected ways.
One more silly question - what is reputation for?