Found out that the Skirt was disappearing when I removed the check mark from "Build Plate Adhesion". The description for that says "Enable printing a brim or raft". It doesn't say anything about Skirt which is to prime the printing nozzle and have nothing to do with Adhesion.
@RickyTikiTavi Thank you for the report!
The purpose of skirt is to prime the nozzle for better adhesion of the actual part, and settings are included under adhesion in custom settings. That being said, the tool tip is definitely incomplete! We will get it updated to "Enable printing a brim, skirt, or raft."
Thanks for the report!