It's also not clear to me that it is ethical to have a punishment be far more extreme than a crime. Sending someone to jail for 40 days for stealing $2.75 seems a little extreme. That could easily turn a poor person with a job into a homeless person with no job.
A fine feels more appropriate. Maybe free rides for those who legitimately can't afford the fare.
Crime in NYC did drop precipitously, but it's not clear that broken windows policing was the cause. It's been studied and debated a lot, but as far as I can tell there isn't a clear consensus. Here are some sources:
I suppose creating an interventionist near-utopia won't be so bad if we don't run into any other intelligent life. The ethics of intervention are complicated enough between humans, so I'm happy to defer worrying too much about the ethics of interfering with other intelligent life until we find it. And other than that, the Culture's post-scarcity near-utopia sounds pretty great, especially compared to the current state of humanity.