Lots of people on here want to knock concepts like the one you are asking about, but in my experience most of those people haven't even worked through those kinds of companies or bought properties, so focus on the ones who actually have (if you can figure out who that is). 

I have clients that have these kinds of arrangements, and while it is easier when an org fills your units, you can lose control of maintenance and cleanliness.

In terms of the second scenario, the upside I see is the option to get a different kind of loan (say, FHA with a lower down payment and other assistance programs for K-12 educators like me) since I'd be getting a new primary residence instead of a second home.

I think there are more horror stories than anything when it comes to those kinds of companies. 

Still, its a great subdivision and there are a lot of investors that know what kind of revenue those cabins should be generating. 

At this stage I do not know if responsibility for necessary termite infestation treatment is determined purely by the articles of association and other incorporation documents of the HOA or are the HOA directors in direct breach of any Broward County, Florida State or Federal laws in not doing anything about the ( apparently widespread ) termite problem in the community ?

You’re making a smart move, and that kind of foresight will pay dividends over time.Now, let’s dive into your question: Is house hacking still a good option in today’s market?

Thats the kind of information that separates a good investment from a not so good investment. 

Beyond that, terminate the tenancy based on your lease (you should have a clause in there that permits eviction for this kind of behavior).

I’d like to trade it for this kind of property in this place.