I mean, presumably the AI wouldn't just be monitoring people sleeping under bridges, but would also be able to effectively cut through tax evasion bullshit, insider trading, bribery, etc.
You're describing a hypothetical world that will never exist. Basically if we solve all corruption and inequality in enforcement between economic/power classes - all-pervasive surveillance will be a net benefit.
It's like pondering hypotheticals about what would happen if we lived in Middle Earth.
If the same monitoring is present on buses and private planes, homeless hostels and mega-mansions then it absolutely is better.