Here is an update. I have completed all the mountains (all handdrawn, really didn't like the clone tool).
I also am working on giving the rivers a tapered look. Color of the rivers is still a WIP.
Played around with the fonts and colors (see Free Hold Society in middlish of the map). Probably will give up on doing labeling for now.
Experimented with the upper left section of the map (known as the Field of Ash), still needs a bit of work.
Reworked swamps, still think I need to improve my technique/style of them. Seem to blend in too much with the woods/forests.
Change the rhumb lines to be more accurate (or at least I think I did).
Also added a scale and cartouche as well.
Click image for larger version. 

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As for the city icons, I like the ones I have . Really dislike dot-representatives. I might change the glow on them though.