Really appreciate everyone's helpful information.

The tourism authority has had some good information in the past about how many visitors come to each island and, of those visitors, how many book STRs.

I've found conflicting information online.

At no time was I informed that what I was doing was going to cost money.

There isn't enough information in here about the current state of the house to be able to advise you, but I would think #3 is a definite no as it seems unnecessary from a cost perspective although that market has scale to accept it.

I am about to buy my first property in Ohio and I would like to gain as much information as I can in regards to the different legal issues of which I can face in Ohio.

The information contained in this post is not to be relied upon.

We don't understand why technology companies like yours who suppose to have live updates would end up having delayed and inaccurate information than our manual check.

As to the buddy I mentioned in Washington state it was the same scenario; he converted tax-free up to their standard deduction but above that he kept within the lowest tax bracket and paid the smallest amount of tax possible.Thank you @Basit Siddiqi for calling me out on this and giving me a chance to address my mistake; it's important people have the correct information.  

It served us well, along with the other detailed information they could provide, to make an informed decision.