I've made decent progress this week. The trail width and dash array now change with the zoom in. I couldn't get the static labels to work properly so I eventually decided to make a circle on each building (appears on zoom 18), when clicked it shows the building name.
I also finally got around to walking (most) of South Pond Loop, I will finish the last bit (south road to town trail) this week. I've drawn what I have thus far in OSM. All that's left to do now is fill in the missing piece and export it so I can convert the .osm file to a .csv and add it to my trails file.