Wow that looks fantastic, Torq! The mountains are stunning, complete with contour lines! - although not sure if you should keep one or the other - I like it anyway.

May be worth playing with the opacity of the fields, by making them more opaque, at the moment they look a little ghostly compared to the buildings and 'brownland'.

The town itself looks entirely disordered at the moment, like a big refugee camp. From the history you've written it sounds like the town was once under a central, military authority, so it ma be an idea to have the underlying 'bones' of the city reflect that by having them quite regimented. The healers and the smelting mines suggest districts individual to each. now the Orcs are in charge, presumably the city is more chaotic, but it might be worth to still have some of the remenants of the earlier structure of the city vaguely apparent to give it more depth?

I find convincing cities incredibly hard to draw, this is looking great.

You've inspired me to have a go at drawing one myself!