I must say this wip is becoming more and more interesting and inspirational.
I think you’re doing a great job.
Regarding city icons, I agree with the others; also I think you should choose between 2d and 3d rather than having both.
Your map style here reminds me to TheRedEpic style, have you seen his maps like this one? Maybe you can get some inspiration for the icons from them.
Yeah, this map is very inspired by TheRedEpic, I want to try and keep it different enough though.
As for the icons, I'm not sure to do besides what I already have for them. Maybe just simple Icons would work better?