I like your idea, but really, most things don't look well thought of. You should finish all your planning first before even considering starting to map/program...
Thanks for your input. I know that there is a lot of content in this game, city/town wise as well as routes, but I haven't spent much time on this project and looking toward the future, this is probably going to end up being done in my spare time, a side project as you will.
At the moment, I am taking more time to design routes that the towns (haven't gotten to a city quite yet#, but it isn't bothering me much.
And to answer your question a bit more, I know everyone would be against this but, I am designing the story an island ahead of where I am and mapping areas needed as I get to them.
For example: Story
Fire Island - it is done to where is needed
Electric Island - it is only partially done #next island for fire starter - early story)
Fire Island - around half done, with only one and a half maps actually needed for the story.
Electric Island - none.
May style for this might not be the best however, it works for me and my lifestyle.
Here is the player's home island
Central Island - Player's home island