Well, I just helped woodencart235 with WorldEdit and I noticed that after I helped him, there were holes that are under the road. Visible from the opposite end of the plot.

Screenshots: http://i.imgur.com/OGSyOqf.jpg & http://i.imgur.com/MOjWIdj.jpg

Hopefully, LogBlock will tell the cause of this, as well as my hopes that this is the only place with the holes under the road. 

These holes really arent hurting anything, and if someone doesnt want them there (if they can be seen from their plot) then I can remove them, there are a lot of holes everywhere under the road and there's no point in fixing all of them if they arent doing any harm.