There is not much activity on this forum so I'm going to take some bandwidth and describe some of my design rules and guidelines.
A little back ground first. After about a year of playing I started a complete redesign. I did not nuke. I should have nuked. Everything was moved at least twice.
I started the redesign with the Simpson house, that I placed in, what at the time was, the geographic center of Springfield. Then I built the residential area around it. This residential area was moved as a whole twice. These were different moves then the ones described in the previous paragraph. Once to the North (away from the beach) with the last SPH expansion. The other was to the East and I can't remember why. Both of these moves were done without the aid of the selection tool. Both were very painful.
I wanted a North/South road to go from Squidport to the end of the map. I also wanted an East/West road to go from SPH tunnel to the end of the map. Also the intersection of these two roads is at the Northwest corner of the main residential area. Note that the East/West road has the buildings in the same order as the main splash screen. The North/South road has Springfield elementary on it. A very dangerous road crossing. The Simpson house is the one with the “$”.
https://i.imgur.com/7QDTRiO.png
The monorail had its own set of rules. The tracks are never to go in the middle of a road. Tracks cross roads sidewalk to sidewalk, if at all possible. There are two cases in SPH where they go from grass to sidewalk. The only two exceptions. Avoid “S” curves at all costs. I don't like the way they look.
In all design work I try to keep to the far side sidewalk from being obscured as little as possible. This is where you see the characters.