Your relo benefits will likely govern this decision more than other factors.

Overall, these measures underscore the federal government’s effort to alleviate the financial strain on those affected by natural disasters.

The first thing here would be the regulations and laws governing acquiring properties, managing properties and selling properties.

Then the tenant should be required to add you as "Additional Insured" which protects you under their policy.

Your primary strategy should be to have the Contractor and all Subcontractors add you to their insurance policy as Additional Insured. 

**Cash Flow & Reliability**: The cash flow can be great, especially since the rent is typically above the average for the area, and it’s guaranteed by the government.

How would an umbrella policy protect against a security deposit related claim?

I feel like in today’s day in age there are so many tools for STR operations and I cannot believe there is no integration for a merchant of sale transaction or some kind of financial app/ software that can take the remitted taxes and pay them to the government automatically.

Also massive cuts to government spending that support recovering economies would not be good for that city.

They do have policies in place, so if you're not willing to go all in, then this is not the software for you.