You have probably found the most confusing feature to explain. Let me dumb it down for you.
The Pin Selected Trip feature only works if you have completed a trip.
First, go ahead and select a trip in the Trips Tab, click on that trip and you will get flown on the map and a red line will appear. Looks Familiar? That red line is actually the exact trip route you took.
But what does Pin Selected Trip do? When you have that trip in red on your screen, play around and click Unpin Selected Trip and notice that that red line goes away. Click the Pin Selected Trip button and that trip is now back on your screen.
The purpose of this feature is to "redo" a trip or use the selected trip as a reference trip. When you do a trip you really enjoyed and you want to do it again with the directions and route line, select your trip from the Trips tab then Start Tracking. Boom your previous trip is red, and your current trip is blue. Use the Unpin Selected Trip and Pin Selected Trip buttons on the Map Options page to toggle the red (previous trip) line on and off, for your off-roading reference. Almost like toggling on and off a flight plan.
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