We lived in Skagway for 6 years 1996-2002. I flew between Skagway and Juneau more times than I can count in those years (Cherokee 6 front seat passenger). The valley north of the runway is wider than it appears and turning around after takeoff or before landing was not a big issue.
As far as air traffic control all the pilots talked to each other and announced their locations as well as their altitude and direction. North bound traffic was on one side of the canal and south bound traffic was on the other side. in one direction you flew at even 1000 foot levels in the other direction at the 500 foot levels, ie 1500 and 2000.
What was very exciting was the weather. Skagway is a Tlingt indian word meaning home of the north wind. You could get bounced around pretty severely and the plane was frequently in dramatic combinations of pitch, roll, and yaw on landing until about 20 feet above the runway when the ground effect would help stabilize the situation.
Without air traffic control it was all VFR. There were many times that we returned to where we took off because the fog and clouds put the visibility below minimums. We flew between the mountains not above them and you dont want to fly into a "granite cloud". When the weather was collapsing you flew as close to the mountain as you could and still turn around by turning toward the mountain. When I asked the pilot why he didnt turn around by turning away from the mountain he explained that if you turn away from the mountain you might not be able to tell where it is once you get turned around. Any way it was exciting and on a clear day the flight between Juneau and Skagway was unbelieveably beautiful.
John Bush