I see there are some recommended companies on here.

As a medium-term rental, you'd be in better position to be connected with Insurance Company that way.  

@Apurv Asthana I usually keep high deductibles and low premiums on all my policies since I wouldn't file a claim unless absolutely necessary...usually I can get things repair at good pricing. 

And if you are need of MTR management services, my company, Island Stays Hawaii, provides premier STR and MTR management services.   

If I put all of my eggs in one basket (Florida in this case), paid off property and a hurricane blows everything away, FEMA is nowhere to be found and the insurance companies take years to pay what little claims they actually do pay, I suffer through it in a blown out house.

From there, I would like to consider a 1031 exchange in the future to acquire more units.My current property management company suggested that they could handle a mid sized apartment building but I would absolutely not consider them for it as I believe they have overextended themselves and communication is lacking.

The learning curve is probably great on importing large quantities or even just large things from a foreign company.

A third party company that integrates with our system.

When I had to switch Property Management companies, they suggested that I do include pets in my rental listing. 

Hiring a contractor to assist with repairs and a property management company to manage rental.