Thanks for the comments and suggestions, I think I'm going to give it a shot or at least take it a few steps further.
I've taken a stab at adding (114) army circles just to see if/how things would fit. Had to take a few liberties combining a few countries (please don't lose your mind/flame me if I merged your home land with an arch rival, etc., no socio-political intent on my part just trying for a workable circle fit) and splitting two (Indonesia in to several parts and Malaysia into Asian mainland and Bornean island parts), the goal was to remain as true to actual political geography as possible. I think the result is tight but workable with perhaps a few more creative mergers in Africa.
The continents aren't balanced in terms of number of territories (see list below) however they are not bad in terms of border counts and I think the territory disparities could be overcome by continent bonuses and perhaps some points for holding certain 'strategic' territories.
10 territories, 4 borders (Alaska, Greenland, Panama, Caribbean)
12 territories, 5 borders (Columbia, Venezuela, Brazil, Tierra Del Feugo [two connections - South Africa and Fiji])
34 territories, 5 borders (South Africa [two connections - Australia and Tierra Del Feugo] , Morocco, Tunisia, Egypt, Somalia)
20 territories, 7 borders (Iceland, Spain, Corsica, Turkey, Ukraine, 'Baltics', Finland)
30 territories, 7 borders ('Holy Land', Syria, 'Caucasus', Russia [multiple connections Finland, 'Baltics' and Ukraine in the west and Alaska in the east), Yemen, 'Asian Malasia')
8 Territories, 3 borders (Australia [by sea to South Africa], Fiji [by sea to Tierra Del Feugo], 'Sumatran Indonesia' [to 'Asian Malasia'])
What do you think?