My 30 year old son lives in Lakeview. He didn't watch Friends growing up - it was a show more for the Gen X crowd. He lives there because he has a great job and enjoys the city experience. It is doubtful he will live there the rest of his life though, and that's OK.
I did an informal study of young people in our Chicago office. Most preferred to live in the city when they were single or attached with double income, no kids. About 90% of the city dwellers moved out of the city to the suburbs within a year or so of having children. I was not surprised by the trend but was by the high percentage.
That's exactly what we intend to do in the spring, although our son will be four next year. We bought right before he was born, though, which kept us in our current townhouse much longer than we would have been able to stay in a condo.
There's nothing at all wrong with our house or our neighborhood (I'd happily send him to the local public school and we would have sent him to preschool last month were it not for COVID), but with both of us working full-time from home, we've almost outgrown our three-bedroom house. We also don't have a front yard or back yard, and a SFH in this neighborhood is way out of our price range.