
and to be frank i haven't even noticed how clear the water shading variations are with all the coloring in the continent because of the names and borders

oh and actually castles wouldn't be visible but cities would be even as tiny groups of dots. after all modern cities are visible from the moon. it's no problem if you don't want to add that it would probably cramp the image even more.
i was just curious about the wall because i didn't read the books. are they any good?
anyway back on track. small map. in the "final say about size" you said a map "must fit within the size guidelines to be moved from the Map Ideas sub-forum to the main Map Foundry forum". while i understand you have designed the large map thinking of the small one i'd still like to see a small version. you say the border movements won't affect gameplay. i say better to be safe than sorry. make a small image solve the border issues and the circles and font and when that's finished gameplay can be discussed. it's really useless to set some bonuses now if they will be changed on the small map.
the font. maybe look at some of the fonts in the book. haven't searched but i'm sure they must have some cool looking fonts.
one other thing i searched the net for westeros and i found the map below. it has a much bigger color variation than yours. it has deserts and snow and dense forests. perhaps you could alter the colors a bit to reflect these things.

edit// one more thing. you said copyright has been taken care of. what exactly did you do? i have a map in my mind but the copyright is problematic. do i just send an email? what do i say? how long do i wait? please pm me about this matter.