So I'm trying to romance Judy and this quest hasn't triggered yet. I skipped time for 24 hours after Double Life but she didn't contact me. What am I doing wrong?

I have seen some people report skipping time from the menu does not always trigger these "wait 24 hours" requirements and you have to have an actual 24 hours of playing time pass (about 3 real time hours). It may trigger if you do any jobs that must start at a specific time and allow you to skip ahead to start the job.

Edit: I was just testing out something regarding triggering the "Chippin In" side job which happens at the end of the "Tapeworm" and basically requires getting to the point where you can trigger the end game mission "NocturneOP55N1". It was after Tapeworm completed that I got the call from Judy for "Both Sides Now" so that may be an unstated requirement for this to trigger. I strongly suspect this is the case as my completed jobs journal history shows I completed the Panam, Takemura and River quest lines in full in between "Double Life and the end of "Tapeworm".