Gunny,
After five years (and counting) in Cubs, I'm kind of new to this Boy Scouting stuff. But, I'm pretty good outdoors through the virtue of my own mistakes.
We just did a backpack trip where the boys did 13 miles in one day in a cold, solid rain. Of the six Scouts, two had done one 15 mile trek before, the other four were on their first trip. Of the four dad's, one is very experienced, I'm OK, the other two were total novices.
All of them had pretty much the right gear. We drummed proper footwear and socks into them. What I think really made the difference is that their dad's were present at teh planing meeting where the experienced packer and I were sharing some horror stories of killer cotton and giving ideas where to get cheap gear.
I've become a fan of resale shops. Got my kid outfitted pretty cheap. Switchback pants are perfect for hikes and outdoors, especially with long john's. Nylon sweatpants for $2.99 at resale work as good as $40.00 hiking pants.
Wal-Mart now carries a good selection of polypropylene shirts and Poly underwear for kids and adults. About $9.00 each piece.
Again, I think it's a combo of training the parents as well as the Scouts, especially the newer year kids.