Of the two maps you're working on, in my opinion this one has more potential than your Central America.
RjBeals has already posted a mini to-do list for graphics stuff - I would take heed of his advice as he generally knows what he's on about.
I like the direction you're heading on, but would love it if you could make the map feel more piratey and treasure-mappy... I really think the map needs something more to drag people in... naming (rather than numbering) the territories on the map will help, and part of me would prefer a single 'treasure island' map with places like Dead Mans Hill, Pirate Cove, Parrots Rest etc. etc. - you could really play on the kitsch/comedy/swashbuckling value
Check out other 'Treasure Maps' for inspiration
http://images.google.co.uk/images?hl=en&q=treasure+map
Before you spend hours and hours tweaking and re-tweaking things, it would be well worth your while thinking through how games are likely to pan out - especially with the victory condition. You will need to ensure that the 'treasure' is equally accessible to all players regardless of the drop, and that it isn't too easy to get and hold early on in a game...
I'm looking forward to seeing how this develops... Keep up the good work
