Should be the easiest to program, not that I know anything about programming.
I'm not a real programmer, but I do have to cook up the occasional bit of script from time to time.
Here's my perspective on assessing how hard something is to code:
First, read through that block of text you wrote, counting the number of "ifs" you used. A simple "if" translates to a chunk of work. A complex "if" translates to a headache and a chunk of work. An "if" that is measuring something not currently programmed, such as which cities are along a route, translates to a huge amount of work.
Second, look at your idea and count all the different outcomes that can arise. For instance, if you have illegal weapons: not noticed, flavor text, flee, surrender, fight, police beating. Something already in the game exactly as you want it. If it's something that's not modeled in the game already, like fines, it's gonna be a lot tougher. And the more general the outcome, the worse it gets, because general outcomes are really a bunch of if's and specific outcomes hidden underneath.
Generally speaking, good communication is complex. When talking to people, you want to convey a wealth of information and different possible ideas with the fewest words. Communicating an idea for programming is the opposite. You want your idea to contain as little information as possible. Computers might be precise, but they aren't subtle.
So don't think about the unimportant contingencies. Not even Toady describes stuff merely for the sake of describing it. You need to be shooting for a specific goal, some exact thing you want to accomplish, an "arc" if you will. You want to achieve that goal while describing the situation as little as possible.
Really, it wasn't too bad until after you made the quoted statement. But past there....