Alternatively you could just not make building housing illegal. the mor regulation you add the more expensive things are going to be and the more opportunities there are for corruption. The harder you make building housing (the more regulations there are) the more expensive housing is going to be. If housing is expensive homelessness will rise.

Alternatively you could be like San Francisco and lard on regulations "meant" to help that have the effect of reducing supply, resulting in a large homeless population, since people want to live there.