So in this instance I takeoff without clearance and then immediately requested landing at JIA.
MS FSX Short Hop Boeing 737
Cecil Field in Jacksonville, FL to JIA (Jacksonville International Airport). From start to finish the entire process is about 20 minutes of video. The reason I do not request takeoff clearance at Cecil is due to what I perceive to be a bug in the game when setting up a flight plan. In many circumstances, even if you move your aircraft to the “Active Runway” when prompted, you could be lined up on one strip and when requesting clearance it asks that you drive your plane all the way across the airport to another strip (pain in the ass).