Yes you take it easy but you should do that when travelling at night My main go to grounds for night fishing was in between two reefs and rather large and dried at low tides in places and once around these heading back to port was another reef in a direct line of travel back. Lucky to have three light houses you could just pick which gave me something to triangulate off. Certainly places you would stay away from at night as you always had to have the ability to get back to port if required during the night.
Having the charts and the good book (variations, current etc) to calculate your heading was a must and the most important thing of all was your compass. I always had very good quality compass and I would swing it in the harbor and keep records as you are playing with your life and those on board. Was building vessels under surveyor back then and before we could hand the boat over and get final sign off the compass needed to be calibrated. Back then this was done with a person that was certified and most times was a harbor pilot. After many trips doing this and the gents explaining the tricks I was doing my own boat. It can be surprising just how much your compass can be out as you would know from your back ground.
Years ago when we were young we did do some crazy shit just to get out for a over night red trip. One rule we did try to keep too was always two boats but sometime even that was disregarded. Down this way that is never a problem as there will be 20 boats next to you.
As to the Swains Scott, I don't think I would even do that with GPS at night