Size and detail is tricky, I had never really thought about how much is in that town until I just googled the maps! Wow, its amazing. I would probably make it a largeish sized map and include some main attractions like:
kwiki mart, powerplant, simpsons house, Town hall/jebidiah springfield statue ...

I found some great simpsons map links here with a google search:
http://images.google.com.au/images?hl=e ... +map&gbv=2

Not sure if its what your after but hope it helps!

Peace,
Ony

Would love to see a map based on Robert Jordan's Wheel of time series. Part of the world map is included in the books and more showing the Seanchan etc could be invented.
Anyways, I'm probably the only fantasy geek interested in it but I thought I would put it out there =)
Peace and Love Ony
ps ...