My son and his friends are 18 - 19 years old, of his friends:
One is DF and attending University
One is No longer a publisher and attending University
One is No longer a publisher and living with significant other
One is a regular pioneer not working or going to school
One is a regular pioneer and gay, but not sure what to do at this point in his life
And then there's my son, a bit of a conundrum. He is close to all his friends. My son is in his 2nd year at the University, works 20 hours a week, and practices Muay Thai. He isn't interested in being an MS, but helps out around the KH. The first few kids I mentioned above had strict JW upbringings and it pushed them away. Which makes me wonder about my approach with my kids. When I was an elder and my wife and I pioneered we had a laid back approach. After I quit, all of the family studies, meetings and regular FS stopped for my family, but they still go to the KH mostly for friends and family.
Born-ins are interesting for me to think about. My mom is a JW. She raised my siblings and me in a strict manner (Mom is a black lady from the south and she "don't play"). All of my siblings except one are out. Many of the born-ins I know who had laid back parents are still JWs. I know a lot of born-in JWs in the Midwest, South, and East coast U.S. and most of them are JWs socially.
In my experience the born-ins (my age and younger) who are still JWs tend to be "weaker" than the converts from my mom and grandmother's generations. I have relatives (Bethel heavies, Sub CO) who are nowhere near as staunch as some of the old school brothers from back in the day. We went on a cruise earlier this year with CO & wife, Bethel heavy & wife, and several other family members. We had a good time like regular (i.e. worldly) people. Perhaps it was because we're all related, but whenever we get together during the year and no one is proselytizing the JW world is forgotten for a moment. I don't know anyone in Legal, but I think the .org will weaken through gradualism and morph due to legalism. Some leave and the ones that stay tend to water the whole thing down.