How does this actually stop homelessness?
Most homeless people, if you fine them money, won't exactly be able to find housing more easily. Similarly, if you imprison them, they aren't suddenly able to find a job more easily.
At least if they’re imprisoned they’re no longer homeless
Most people experiencing homelessness are approached repeatedly by workers hoping to get them into programs that will provide them work, housing, mental healthcare.
There's a lot of complexity, like people who appear homeless but do have a place to sleep, but appear mentally ill.
For the most part, people in these situations are not looking for work or housing.