Alright, this is my first map, so have some patience

My main goal for this map is to create an expansive map of the American West that captures the essence of the massive territorial expansions of the 19th century. While regions/continents are still important in this map, equally important are the expeditions and trails that helped shape the history of the nation. In addition to the expansion and conquest theme, there are two additional elements that I want in the map: Native American Settlements and Hazards. My idea for the Native American Settlements is to have the capability to bombard any trail/expedition-linked territory within their region, thus hampering that expedition or trail. In addition, various Hazards in historically and strategically key locations provide additional obstacles, as they lower the troop count in that territory by 1 per turn. Combined with the natural obstacles of the map, this should make conquering the map a challenging and interesting pursuit.
Now for the basics of the map:
Territories: 51 total territories, with 8 neutrals, for a total of 43 starting territories.
Native American Territories: 4 Native American Territories that can bombard any trail-linked territory within their home region.
Hazard Territories: 4 hazardous territories that lower the troop count within that region by 1 troop per round.
Regions/Continents: 7 geographic regions, with varying degrees of risk/reward for holding that region.
Trails/Expeditions: 6 historically significant expeditions and trails, with their own challenges and rewards.
Barriers: A variety of natural barriers throughout the map.
I'm also going for an aesthetically pleasing and interesting map. So far I've added some example artistic "doodads" in various regions (Pikes Peak, Great Falls, Oraibi, etc.) to give you all an example of the direction I'm aiming for.
Now, I know I've just written quite a bit about this and showed a working draft of what I've done so far, but this by no means means I'm locked in to one particular direction. Most of the bonuses/regions/ideas are just rough sketches of what I'm aiming for, so feel free to tear any of that apart. I just wanted to get a good start to kind of illustrate what I'm going for. I'm open for any and all suggestions/revisions/criticism about any aspect of gameplay/graphics/theme. I don't mind revising at all, and I'm anxious to hear any ideas about this.
Now that all that's been said, what are the thoughts on this?
Previous Version:
http://img29.imageshack.us/img29/1047/m ... nycopy.jpg Version 1
http://img175.imageshack.us/img175/443/ ... oncopy.jpg Version 2
http://img691.imageshack.us/img691/8721 ... n1copy.jpg Version 3