I also wouldn't touch hilltop with a 10' pole. struggled. old homes, over budget renovations, lots of issues. realtors push people here since it's the only place cheap houses close to downtown can be good but homes are 1900-1920.

Plenty of STRs that perform just as good as the pool STRs because they have a great design, location, or other fun amenities that have less liability and headache.

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

We only disagree on what is basically a customer service issue.

It is located on a very scenic setting.

Where is your property located?

There are a lot of good things about Wyoming LLCs, but the favorable Wyoming laws don't matter as much because the state you are in will apply the laws of the state the property is located in. 

After I did find the coverage I am getting notifications from the insurer that a long litany of minor issues must be addressed (at almost every house). 

We agreed to address the issues left by the previous tenant and you did not want us to handle it.

Let them know that they may wish to look for another place if that is going to be an issue.