Thanks for the feedback everyone! I can usually find time to work on this on weekends or Wednesdays.
Notes:
I took the legend and title out for resizing and will probably put them in a column on the right, then have enough space to put some flavor text about the map's history. I've resized the large version to just fit at 1,000 pixels tall. I scaled it down 10% to 900 pixels for the small version before realizing the maximum height for a supersize small version is 650 pixels. Given this realization, I don't know whether this concept can be completed at all without significantly compromising the design goals. I will reevaluate the project over the next week or two pending feedback and contemplation. TBH I am pretty crestfallen about it after being inspired by my favorite maps First Nations Americas and Eurasia.
Unaddressed Concerns:Small version is too large
Some territories need to be reshaped a bit
Legend, title, rules to be readded (expected in column on side)
Considering transparent white circles behind troop numbers
Considering using white text instead of black text
Updates:
Water routes adjusted to take up less space
888 Tested on 900px tall version.
Removed legend and title
@Seamus76 - I am using Photoshop CS5.1 for this and am mostly familiar with the tools. I do wonder how it's best to organize layers. Right now my layer groupings are horizontally integrated (text, region backgrounds, meta/legend, borders) instead of vertically integrated (continent, region, territory). I'm not sure which way was better, but I had a lot of tediosity with my approach.
This is the 900pixel tall version with gray numbers. I chose gray because I think it's the hardest color to see.
http://i.imm.io/10eqz.pngHere it is 650 tall with some numbers applied.
http://i.imm.io/10fFc.png