It looks like the original poster may be accustomed to packing light and quick, so his own shelter in the past has been just the 5x7 tarp. That works for one person making short trips where the weather forecast can be checked just before leaving. For one person going light, there are options if weather gets bad -- hiking out, heading someplace with more shelter, etc.
But on this trip, it looks like a "troop" is going, so I am guessing a group of scouts. ...and they are taking 7 days for a ~40-mile trip. Slow and steady.
In this situation, Trenton should probably skip the ultra-light mode. Since the troop is moving so slowly, a better and heavier tent would be welcome in case of bad weather. If Trenton has an ultralight bag, using the tent adds warmth, so what was ok under a tarp or under the stars, will probably work on chilly nights inside an enclosed tent.
As for mosquitoes, he didn't ask, but I'll add this: Just take along an ounce or two of full-concentration deet. Using it sparingly, even if the bugs are bad, it works. For overnight, all you need is to apply a little to the face and maybe hands, since those are the only exposed parts. That works, even sleeping out in the open ...which is what I always do except in foul weather.
