Alrighty, Tyler. I have showered after bball and feel refreshed, so I will take on ur map

Firstly, I realize that you will probably take Benn's idea and run with it, so this could be unnecessary, but still …
One, the entire map is, like I said, very isolated from part to part. The ones on the right are good, but the northernmost bonus (you still need to name these, by the way) is so far away from the other ones it's like it gets lost at sea. This also creates a humongous flaw in the gameplay. Alright, say I drop with Chenton, C. Charles, Oyster, and Red Bank. I'll drop all on Oyster, take Capeville and stop there after forting all to Red Bank, Capeville, and Oyster. Next turn comes, and with my bonus I take the four northernmost ships (still need to name 'em …), then fort all to the chokepoint ship (god it's hard without names). Now I have 15+ on there, can place my 7+ with the (ridiculous) +4 bonus I got on that ship, and take all the ships and V. Beach. With 15+ there and the ability to bombard 3 other places, I have won the game with a little troop concentration out west.
Point is, the bonuses are both ridiculous and detached from one another. See WM's Bonus Tool
here (.zip download file) and fill accordingly. That's a start.
About the graphics — while I do like the feel of the colors, the entire map is drawn out vertically. I know you traced the real borders from your source picture on the minimap, which shows how they really should be and looks oh-so-much better. Speaking of borders: if you really want to be cheap, which you seem to be doing here, hold shift while drawing your outline lines for a straight line. Please do! Also, you should probably redraw all the borders making sure to connect them and that they don't overlap twice and such like James City and Norfolk W. do. Another thing is that the island between Suffolk and Norfolk is unnecessary, IMO. The one off Pequoson is a bit better because it's bigger, but still. RJ's Charleston map could be something great for you to check out — although it is in a different setting he did a really good job spacing the separate islands (great map, btw). The ships will be needed to be redone for copyright, most likely. Also, when you fill in the islands use the paint bucket tool, don't just draw it in there like it looks like right now.
Just a start — got some ways to go

. I suggest taking Benn's idea, by the by.
.44
P.S. your army circles will be too small (I think)