I mean, maybe some people are homeless by choice, but some are due to misfortune and poverty. Using technology to turn a blind eye to poverty in our communities seems bad. Also you may trip over a homeless person.
It would defeat the entire point of having them: As an example why to obey. It is not like you cant scale a tax with housing requirements. Could give them jobs too. It would take a bit of getting used to but if the only thing a person wants is drugs their potential productivity could be 10x that of ours combined.
You may trip over a homeless person if you can't see them.
Also papering over social problems means those social problems will bite you in the ass eventually. Never underestimate the power of a bunch of desperate people.