Good job, Ryan!
Regarding your comment of:
"I'm not even sure I have the desire to see 'all teenage boys go into the backcountry.' "
I agree, this isn't for everyone. However you did point out some important factors that influence what kids do today. For most of us here on BPL, we would like our children to participate in our outdoor passions -- but you cannot force them to enjoy it. But the factors you point out are often detrimental to raising kids with "character."
Over the years I have seen so many questions posted from parents wondering how to handle their kids, and friends often ask me for input on difficult situations. My answer usually is, "Who is the parent," because the situations involve the need for someone to make a decision, and that is the parents' responsibility. Too many parents allow their children to make the important decisions.
I have two grown children and am extremely proud of how they turned out. Never had a problem with either, and they have always been 'high achievers' in anything they tried. Since I was in my mid to late 30's when they were born, often I was a generation removed from the parents of their friends. So I really saw a difference in how their friends were raised versus my kids. Perhaps I had an advantage of nearly 20 years of life experience as an adult, before they were born. But as parents, their mother and I set the expectations. We refused to deal with the things you pointed out; (culture of entitlement, peer influence, etc.). We set the standards and raised them to gain self-esteem for what they were, not what the rest of world was. For example, there were no video games in the house -- they weren't allowed. Television was limited and had parental control -- the kids thought is was normal to sit together at night and talk; they also thought it was normal to read a book instead of watching TV.
We took the kids camping starting at age 6 months. This was our vacation every year. And we did not bring things for our own entertainment, we spent everyday together doing family things. Of course, everyone had some personal time everyday, which was usually reading a book.
When they started school, they were required to join an activity during the year. What is was, was up to them -- sports, music, clubs, scouts, etc. Joe played sports. Nicole played sports but hated it, and soon got involved with cheer leading and then dance. And every year between September and June most of our time was involved in participating in these activities. We had to give up a lot of our personal wants/needs so we could properly raise our kids. Raising kids was our most important and primary job. And it wasn't always easy.
The other thing we did is set standards of performance for school, activities, and personal conduct. The standards were not some arbitrary goal of all "A's" in school or winning a race or a competition; but that they gave it their best effort. By the time they started junior high they knew right from wrong, and could not be swayed by their peers.
To me the important thing is for parents to be parents. It doesn't matter if the parents hike, or go camping, or enjoy other activities; the important task is to raise kids with character. And I think Boy Scouts and Girls Scouts build character. Both of my kids were in scouts for a short period of time. These troops were in suburban areas and the outdoor activities were nominal. They opted out of scouts because they would rather go camping and hiking with us -- even though most of their friends looked down at such family outings.