Here is the wiki page for multi-sided tokens of each region from Rollable Tables method, that The Aaron suggested, <a href="https://wiki.roll20.net/Card_Decks_and_Rollable_Ta" rel="nofollow">https://wiki.roll20.net/Card_Decks_and_Rollable_Ta</a>... Different but similar option, if each Territory was a Token then you could use TINTS. <a href="https://wiki.roll20.net/Token_Features#Tint_Color_" rel="nofollow">https://wiki.roll20.net/Token_Features#Tint_Color_</a>... Another very quick way is the Roll20 drawing tool, <a href="https://wiki.roll20.net/Drawing_Tools" rel="nofollow">https://wiki.roll20.net/Drawing_Tools</a> (similar to the MS Paint you were using, no paint bucket fill but there is filled-shape drawing). I recommend the Polygon drawing tool with both the line-stroke and the fill-color. Would that work? Gauss is one user who has run some Tanks games on Roll20, he or other users may come along to give some tips and tricks. Another idea, ever used Flags or Pins placed on the territory? This could be easily done with Tokens (uploaded or from the Marketplace), or even Card Decks. I would like to recommend Hapke's pins from the Marketplace as an example, <a href="https://marketplace.roll20.net/browse/set/833/old-" rel="nofollow">https://marketplace.roll20.net/browse/set/833/old-</a>...