I'm looking for some suggestions for labeling a a town that includes residential and urban areas that are extremely dense. So far, the only progress I've made has been by using the "reduce font size" feature in the labeling options, but it has still proven to be unsatisfactory and the font reduction engine seems a bit non-intuitive and poorly prioritized. It doesn't make sense to make the size very tiny everywhere, because there are portions of the map that are not dense at all, and lend themselves to a larger font size. I've attached what I have below, and it's a complete mess. Are there any better ways to label a line feature class that is at times incredibly dense?
Below is the old map. Their labeling seems very intelligent, and almost annotation-like (labels look hand-placed with intuitive leaders), and I'd ultimately like to get it looking close to, or exactly like that if I can.
I am using ArcGIS 10.3