I have been using Sass for about half a year now and have absolutely fell in love with
sass --watch Desktop/parent/project/css
sass --watch Desktop/parent/project/css:Desktop/parent/project/css
In case anyone else encounters this problem, I have found a workaround by simply navigating to the directory I want to watch (via Terminal) and then executing a watch on the current directory like so:
sass --watch ./.
I hope this helps anyone who runs into this problem.