Cove City (Could use some advice on design)

[anomiecoalition]

Hey all - Couple friends of mine are working on a novel and have asked me to make a city map for them. They've given me some broad strokes, but I get to fill in most of the details of the design.

At the moment, i'm trying to lay out the city walls...its a decaying city with crumbling walls that have not been maintained. So, I was thinking about doing a crumbling outer wall and then a smaller wall around the "old city".

Could use some advice - I'm thinking that the outer wall should in theory include part of the river...but doing so kind of messes up the composition since it gets so close to the border and I wanted to have little settlements outside the city walls. Wondering if anyone has any thoughts one way or the other.