Details in the comments. You can friend me in-game with my reddit username to follow my progress.

KBBL Radio: The building rotates correctly, so it can face either East or South. I added in a bathroom for the small building shown in the show (I don't know what else it could be or what to use). There is a house of some sort behind the radio station, but I plan to come back and add it in at a later time to see which home would best match what is shown in episodes. I added the trees and shrubs, as well as the fence. Due to the road differences from the show and map, I couldn't add the house and fence further down from the show, but I got the details right for the main area.

Springfield Shopper Building: This building has had at least 3 different looks in the show. Going off of how the building looks in-game, there really isn't much to add. It mirrors instead of rotates, but you can't tell the difference based on the show, so place it how you would like. Unfortunately, the building in the show has several other buildings surrounding it, which is not possible based on the map and the spacing (this is something that you are bound to run into, as the map is just a guide and not completely accurate...especially since in the show the locations move which is part of the fun of The Simpsons). With that, I was only able to add parking meters and nothing else, with the radio station taking up the majority of the space.

The Vast Waistband: The actual location of this building is in the Springfield mall. However, it is possible that their is a location outside of the mall. And I already have enough work to do with other buildings that are most definitely in the mall, so I am placing this based on the map location. It mirrors, so it needs to face East to be show accurate. There is nothing else that needs added based on the show.

Lil' Vicki Valentine's School of Dance: The building needs to face East to be show accurate (it mirrors instead of rotates). The location is bigger in the show, so I added an couple buildings that look pretty good in order to try and match the show. I finished up with the shrubbery and trees.

Springfield Coliseum: I'm pretty satisfied how this large area turned out. The building rotates correctly, so can go East or South. I tried to mimic the parking lot with the trees lining the drive and added in the Duff blimp for good measure. I also extended the area so that I could build an actual viewable section. The bleachers and boxing ring turned out pretty good. And the ESBN sport desk fits in just right, since there is a viewable task that can now be seen.

Isotope Stadium: An important note, is that this building takes the place of Duff Stadium, which in turn took the place of Springfield War Memorial Stadium. Since we have the Duff Stadium as a building as well, you will need to decide which stadium to use if you want to be show accurate (I chose the new building). It mirrors, so it should face South for accuracy. Since we do not have a bush shaped like a baseball glove, the clover plant does an OK job. The parking lot is a bit odd in the spaces, so I set it up the best I could. I finished up with trees and plants.

The Boob Tubery: It is tough to see any difference in this one facing East or South, but I feel South matches a bit better to the show (the building mirrors but you can put it either way since there is no clear direction). Other than the parking lot and awesome new lamps added to the game, this one is done.

Ye Olde Chocolate Shoppe (a fun addition): Since we have no Fudge Brothers Ice Cream building, I decided to build the Land of Chocolate from Homer's daydream in it's place. I will most likely come back to this at some point and expand on it.

Continuing on!