This mission is timed. The timer is the fuel gauge that is located under the HUD. The goal is to use the Skimmer and collect all the checkpoints before the plane runs out of fuel. The checkpoints are scattered all around the Vice City Mainland, exception of Fort Baxter.
To complete this mission the player must:
Locate the Skimmer (behind the film studio)
Drop flyers around the mainland, collecting the checkpoints in the process
After the cutscene, head to the back of the film studio, where you will find the Skimmer. Enter the Skimmer and get it up into the air. Fly into the Vice City Mainlands and pick a checkpoint. Once you fly through a checkpoint, locate a red checkpoint near you and fly through it to complete a "set" of the checkpoints. Do this over again with a new set. Once you collected all the checkpoints, the mission is complete and you'll be rewarded $2,000 and the Skimmer.