UBI removes the risk.

>We're really talking about finding ways to give structure and meaning to those folks, the large middle class in America.

Firstly I disagree that people need baby sitting. If they do then that is a huge cultural problem. The beautiful thing about UBI though is that your statement won't matter because the slightly more industrious will round up the bored and make projects and people will partake because it gives them meaning. I think you are underestimating the power of the crowd.