You're thinking to buy a rental property and use the rental income to supplement the travel kitty. 

I am new to this, and I am hoping to supplement my current income so I don’t have to work so hard in the hospitals.

It's very user friendly, free, and gives you coverage nationwide

So for those I use the American Water line coverage plan.

Yes LLC is a "coverage" by definition of a legal entity which is not you, and it doesn't matter if the liability is triggered by an STR guest, an LTR tenant or a handyman working there etc.

Furthermore, unless you set up the property insurance correctly, you could end up without coverage in the event of a claim if the property is deeded in the LLC and insured personally.Happy InvestingDerek Dombeck

These can be financed if a full remediation has been completed with the engineers report and insurance coverage can be bound.

I went to a broker to get new coverage, and one of the first questions asked was if it has asbestos siding. 

These would be a supplement to your BHA and also provide cash flow once you move on to the next duty station. 

I'm trying to determine what coverage levels I really need to have.