We have talked about things like this.
Please sit down, think tranquil thoughts!!
The truth is that many if not most of the Troops that I deal with are no way prepared for this sort of an outpost.
As you are aware the District I serve is next doors to the one you serve and Car Camping is the rule. Many if not most of the adults don't even own a backpack. Those that do rarely if ever use it!!
Of the 15 Troops in the District that I'm in, I'll bet that only two or three have the equipment or the skills needed to participate in a "Real Outpost".
Even the Guys who participated in the Powder Horn a few weeks back are not what you might call great outdoor types.
So maybe this Outpost might serve the needs of those who take it, if it were more of a Training Hike?
Set up different Learning Areas along the way.
Without spending much time and off the top of my head:
1/ Boots and clothing. What the best dressed hiker should be wearing.
2/ Tents and alternatives (Leave No Trace?)
3/ Back packing stoves, how they work, what they cost.
4/ Food Glorious Food. What the well fed hiker is eating.
5/ Don't get lost. How to read a map and different compass options.
6/ Buy the right pack. Explore the different kinds of back packs.
These posts could be along the route.
Doing them at night might be different.
Just an idea.