The broker is also the property management company, and they believe there is some room for a rent increase.

That's a cool company name 

The one thing I did find out when I had a management company manage my property a while ago is that there are people who rent properties full-time during the off-season at a greatly reduced price.   

I'm a former software engineer that built and then sold a company.

I’m currently looking into moving to New York City, where I would like to learn about the market and continue flipping houses.

Proper is a big one, very comprehensive and expensive (we have this), Foremost, CBIZ are others.Many insurance companies now offer STR policies.

There is also a large restaurant company here that I have been told needs rentals for a shorter term but pays very well to house staff that they bring in from out of town to work for them during high season.

Then ask why the property tax rates for hotels on Maui hasn't increased in over two years, yet they continue to raise it for STR's as well as non-owner occupied residential properties.

This particular LLM that uses NLP was created to summary forum conversations.Having said that, I realized BP doesn't need to build AI, because these company can query the result.

You may want to start off with a turnkey company to learn the ropes.