I think he meant the HOA's insurance (including liability) for the common areas of the complex. If the HOA's insurance found out that an HOA board member or property employee knew about a residency violation, they might have grounds to cancel the policy, which would just end up costing the HOA money, which would raise the monthly dues of all owners.

Your (as the hypothetical owner of an apartment unit) insurance cares about whether you are occupying the unit as you said you would. I'm sure you can purchase a policy for primary residence, long-term leasing, and short-term leasing. If you're violating your policy, it could be declared void at any time, in particular if you ever make a claim.

If I were a good insurance agent, hypothetically, I also wouldn't write an insurance policy for short-term leasing in a property where I suspected such use wasn't allowed. It would probably be in my best interest to get proof from the potential insuree that such use was permitted.

As for that rebellious streak, we're talking about an investment here, and ways that people might be breaking voluntarily signed contracts in order to make a few extra dollars (the real-estate agent should offer the HOA terms to any potential seller, and then you sign the HOA contract when you purchase the apartment). Also, I prefer disruptions to business models, not disruptions to living arrangement. As mentioned elsewhere in this thread, there is no upside to the other residents, it's all a nuisance to them.

As someone else said: The HOA representative should care about the HOA's insurance. If there's insurance covering e.g. common areas, it is problematic if the insurance does not cover short term lets and units are used for short term lets, because the expectations of damage from places e.g. rented out as party pads would be far higher than otherwise.

But this also means your insurance company should care, as depending on your policy, if your insurance company would be on the hook for damages not covered by the HOA insurance, it is very much in their interest to ensure that you are not doing anything in violation of HOA rules that might affect the HOA insurance cover.

So ask forgiveness all you want, but realise that your insurance may not be worth the paper it is written on if you break contracts that might affect insurance cover. And that's potentially a very high cost to pay for a "rebellious streak".

> You've clearly got a bit of a nanny mentality about this.

How is espousing that the right to swing a fist ends at another's nose "nanny mentality"? An apartment is in a shared property structure, with rules contracted into voluntarily, and in close proximity to the property of others. Insurance is offered as a contractual arrangement. No-one is forcing you to buy an apartment, but if you do so on the basis of a legal agreement around how you will use it with the co-owners of the building, breaching it justifiably attracts sanctions.