People would rather leave those on the streets to do whatever they want, including settling down on the street, even if it means more suffering for them from the weather and danger from criminals outside.

Instead of seeing laws that keep people from the street as empathetic (because you force them to shelter), they are seen as cruel. Of course lack of enforcement sends a message and further discourages people from trying to find an alternative. Year by year this gets reinforced and it will be that much harder to fix the problem.