Board Game Illustration

We need completely themed out illustration of a board game graphics. Attached is a very rough layout of what we are after but wanting original comical graphics of buildings and landscaping in all of the white space. The idea is that there are different drinking venue buildings with foot paths connecting them all. Not sure if buildings that are better to be flat or 3D with a path enters through one door and out another or just past the entry of the building. I have attached an image of a segmented building that I think the idea of removed walls to see interior of venues will be interesting although the image isn't the right look it shows the exterior and interior, a possible idea but can be thrown out for better creative direction. Potential for box design in the future too. This board game is a drinking game needs to be designed to appear to college/university students and people the aged between 18 to 25. Again attachment is just photos to mark space not what we are looking for in design. Need to bring this game to have a catching retail look! Most creative input and suited illustration abilities will be awarded job. Bring your creative ideas on where you think we should head with this project.