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> the discontinuity between the city’s eagerness to legislate and its recalcitrance around enforcement

For consumer-corporate disputes, learning to leverage New York's regulatory state is a bit of a superpower. Basically, sending in a written complaint with the regulator copied and then having them open a regulatory-investigatory file is real leverage because even if you're full of shit, it's going to burn legal dollars on the other side. That, in turn, makes a letter to the company threatening regulatory escalation as the next step land seriously.

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NYPD parking on sidewalks is more of a "who watches the watchmen" problem unfortunately.
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It doesn't have to be! Parking enforcement wasn't always within the NYPD's remit. Until 1996, NYCDOT was responsible for parking enforcement.
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Sadly, even if this were the case, there is no mechanism for one NYC city agency to fine another one.

This is why the sidewalks next to city parks take forever to get shoveled after a big snow storm.

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I would settle for a bit of towing, or even just fining the individual cops who park their personal cars on the sidewalk. Parking of city-owned vehicles is also a problem, but the former seems easier to enforce per your point.
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Not to mention completely opaque tinted windshields and windows, and intentionally defaced or corroded license plates..
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Corruption is part of the job description, for the NYPD.
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Not a NYC-only problem though. There are tons of federal, state, and local laws that go under-enforced or unenforced. Legislators love the performance art of writing these kinds of popular laws, but law enforcement often doesn't care enough to enforce most of them. In this case, the website says the penalty is "starting at $525" which is basically nothing to a corporation, and nothing to the police/government. So you can file a complaint but it will probably go to /dev/null. After a year of this people will give up on even filing complaints.

What needs to happen for rules like this is: 1. the complaint should be easy/automatic to validate and rule on, 2. hard for the company to appeal and stonewall, and 3. the fine money should go to the person who filed the complaint as a bounty to motivate people to look for violators.

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Naturally. I mean only that NYC is an instance of this.

(It's worth noting that the city does sometimes enforce new regulations well, and in a way that the public is aware of. For example, businesses in the city are required to accept hard cash as payment, and the penalties for not doing so can be significant. Friends have told me that the city is very proactive about responding to those complaints. Anecdotally, the city has also become much better about responding to some forms of illegal parking and idling over the past few years. It certainly helps when the incentives are aligned, i.e. the cost of the enforcement program is supported by the fines collected.)

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525 bucks per cancellation sounds like a lot to me tbh
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It's not clear why enforcement would be needed necessarily.

Assuming that you pay with a credit card, I would assume you could dispute the charge on the basis that they're violating the law and win any faceoff immediately on that basis.

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If the business simply doesn't offer click-to-cancel, so you haven't actually canceled your subscription, how could you successfully claim the payment was made fraudulently? The law doesn't mandate that you can unilaterally exit any agreement, it mandates that businesses have to offer an easy way for you to do so.

The example of a yearly subscription paid monthly should make this obvious. You can't exit this arrangement after 6 months and expect to simply not pay the remaining 6 months, as the contract was for a whole year. All this law does is force the business to make it easy for you to cancel any auto-renew for a second year. But if the business doesn't do that and you dispute a payment, how hard do you expect your bank to work to figure out if this payment was for a part of the original contract, or for an auto-renewal you should have been able to easily canceled, but haven't?

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Surely we agree that paying with cash or a debit card should entitle you to equal treatment under the city's rules and laws.
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I've also been disappointed by the lack of enforcement, and it's not necessarily for violations with little harm.

Failing to provide salary transparency in job postings is another common one with zero enforcement.

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