Specifically addressing your questions/comments about night watch:
I counted a minimum of 4 people. That divides into 2-hour shifts for everybody and from 2200 – 0600 allows for 6 uninterrupted hours of sleep. If you cannot get more than 50m with a ground location why not put your watcher on the roof? I’m unaware of what was at the end of your 50m radius but if it was not solid then your watcher could at least improve their ability to hear by being elevated. If it was anything but dense forest being up high would allow notice of movement through brush/crops even with only starlight.
Finally: Since you did not mention any other security preps it is logical to think you did not have them. (What sort of 2- and 4-legged fauna do you have in the area? Based on that info I could determine if rattlers or some sort of tripwire device would be better to use. Of course, I’m guessing you know how to make ankle-biters out of shotgun shells but will decide if/when it would be appropriate to use them.
Understand, I’m not trying to tear apart your AAR or pull apart your exercise. It’s just that certain things must be presumed unless the information presented shows differently. Your report suggested all of you were awakened at 0240, not that one of you awakened the other 3+ with a report of what had been heard and where it came from.
Yes, playing in the woods is great fun. Sometimes I do it to practice/test/improve on only one issue and just lay back and savor the outdoors for the rest of the time. But you opened the can of worms by saying this was to practice bugging out. Be glad I did not go into Honey Badger and Soutie’s performance with Troll Trace.