Well lets see what we've got here...!
Regarding the Visuals:
I like the simplicity of this map, visual wise, though I think it still needs some work. The recently Quenched map of Portugal was a very 'simple' map to the eye, but the way it presented its simplicity felt a little more polished than this current map.
Regarding the textures, as someone mentioned...they feel a little odd. I'm not sure the 'painted wall' texture really fits this map. What other textures could you experiment with?
I'd maybe nudge some the names so they aren't so close to the army circles (I.E. Neb. on small, Badlands on small). Also you are going to have some troubles with New Hampshire and Mass.'s coordinates (3 digits) perhaps overlapping the name, which is something we'd like to avoid. Also look out for Vermont's 3 digit coordinates overlapping N.H.'s. Watch New Jersey's overlap of name also.
I like the use of both flags as a background, but the where the 'flag ocean ends' when it meets the legend, the map looks almost unfinished in this aspect. I'm not sure how you would alleviate this, but the sudden change from the flag ocean to the legend is something to look at.
The river right now feels drawn on, and very un-river-like. And like another user mentioned, the bridge image doesn't quiet mesh with the map.
I see you also use a number of decorative images around the map, but for the most part I'm not a fan of these. They seem to take up space, without adding much to the map. I'd maybe be in favor of removing the canon, bugle, and whatever is above Grant's name. The swords in the name seem alright, though I'd maybe consider moving them behind the title and making them bigger.
Regarding the ships in the water...the current images don't fit with the map. They feel too much like a real life image, which doesn't quite fit this theme. I'd consider alternate images. I also dislike the 'little legend' at te bottom of the map, and how the ships are on it. Also eventually the red connecting lines should be spruced up, as they glaringly stand out and look crude.
The legend feels a little chaotic, especially with the overlap of territory names into it. I'd almost consider looking into cutting off a few pixels on the left side of the map, (as you have some territory space that isn't really needed), to create more space for a seperate legend.
As for Game play....
The capitals aren't a part of the 'Key Cities' bonus, are they?
I like the bonus tiers you have, with the division leaders each having a bonus, along with the collective having a bonus. I also like the inclusion of the key cities bonus, though the north may be at a slight disadvantage as to where they are located. The capitals are similar to Anhk-Morpork in Discworld, and will he contested and a nice early foothold. Side note, capitAls
The rest of the game play looks pretty standard, but good. The bonuses seem alright, but I'll look closer at those maybe later.
Good work, keep it up.