I only skimmed Etienne's post because I'm lazy but:
In regards to gold making: Back in the day city-wide bashing groups used to be a thing, which gives non-PKers a chance to contribute and earn favours/rewards (credits) in this way without actually needing to PK. In my opinion this is a good way to get people communicating with each other. There are also city-credits which the leader owns that can be transferred as unbound and then sold on the market. I'm not sure why you're relying on houses and shops as the sole source of income.
In regards to "people will raid off hours": It seems to me that many people would find that boring. The rewards to me don't seem so huge that people would solely focus on off-hours raiding, because where is the fun in that?
In regards to "people can raid now": Well... Technically you can... But why would you? There's no sense of victory in raiding anymore. People would just exit the city, you could sit there for hours killing guards but they will be back at no cost.
I dunno how the map coding works and etc, but for areas with special exits/entrances/whatever, is it possible to change PATH FIND so it takes you to the room containing the special exit? Like for Strengmire, it'd take you to the room with the gate.
Currently it just says "you are unable to find any way to that area from here."