Kansas City Web Idea

Haven't posted in TOO long! I've been trying to learn some new stuff, so I started a project where I can work on several things at once:

1. Learning how to make better websites
2. Getting better at working with illustrator and photoshop
and 3. Getting to know a little bit more about the city I live in

So here is what I've been doing in illustrator in my spare time, and then I'll explain for my own benefit below, because no one reads this.

 Alright so I'm thinking about making a site of an illustrated Kansas City. Each building or icon or whatever it is, will have a pop-up with a brief history of the area or site on it...
I'm playing around with a few different ideas.

a. STYLE - The orange buildings above get less proportioned starting from the kauffman and going counterclockwise. I'm trying to decide how "cartooney" to get with these.

b. COLOR - So most of these are orange because i was thinking about having a white background and grouping areas of town into certain colors (downtown sites are orange, rivermarket sites are red, etc.) But now I'm thinking as I get further I may want different types of places to have different colors, for example architectural landmarks are purple, historic sites are green, and residential areas are blue.

c. GETTING ABSTRACT - Some places I want to have icons representing the site or area, especially when the idea of the place is more meaningful than its actual appearance. That is why the Disney house above is just a generic house with a fantasia hat on. So Im trying to decide if whole areas should get icons, like one that wraps up 18th and vine, or power and light...

d. GEOGRAPHY - most of KC is in a pretty good north to south line, but there is some good stuff east to west from us, like the Truman home, the sports complex, kansas speedway, blah blah blah. I don't know how I wanna deal with this yet, since I want this to scroll up and down. hmm.

Thats all for now. Kinda wordy, I know.