This is a good discussion. This has been a big issue in the flying world too. Airplanes now are EXACTLY on the charted airway, not just within a few miles of it. This caused a head-on collision down in Brazil between a 737 and an Embraer jet. A lot of restricted airspace violations come from setting the destination waypoint and not bothering to look at what is between here and there.
I like to use OpenCPN which allows very easy point-and-click setting of waypoints. I do not couple the autopilot. I like to stay in the loop and do the cross checking and corrections myself. One other thing to be way of – especially on mapping GPSs with small screens, is a lot of things vanish when you zoom out. The entire crew of a boat in the race to Ensenada (iirc?) died when they plotted a course through an island and apparently they all fell asleep. Their tracker showed a ruler straight line right into the island that would have gone straight to the finish line. Joe Della Barba Coquina
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