So I got as far yesterday as extending the road context into 5 different contexts and schematic families, Road_End, Road_Oneway, Road_Corner, Road_Threeway, Road_Intersection. Not going to lie, I don't really like doing it that way, and I took a break to rethink it. It's not just placing the schematic, but also setting the facing angle correctly, and it's getting a little over my abilities. Let me know your thoughts on how you think it should be built. Either way, we'll probably have to invent a new file structure for pasting furniture schematics

Alright, with a little bit of distance, I'm thinking we're going to have to probably just put all building schematics in a folder called "Buildings", then also add "Furniture" and "Roads" as separate folders as siblings. Originally I was thinking something along the line of putting furniture within the "Highrise" etc. context, but I noticed you broke buildings into "Offices" and "Apartments" so that wouldn't really make sense.

It appears that WorldEdit now can do pasting directly, so for the time being I'll be working on 2 things before getting to roads: Rotating pastes and using WorldEdit to paste.