Does he not cover that yet?

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

I'll just add, you need to prepare the scene before taking a picture.

In the first 10 days listed on Airbnb, the STR rental revenue booked covered the entire mortgage.Lessons learned?

I would look at it in terms of whether you can afford a worst case scenario where you're covering the deductible and have a credit line or cash to front the re-build cost and getting reimbursed from insurance afterwards.

Cash-flow is for "keeping the lights on" as in covering operational expenses to defend against any need for additional capital investment. 

If your property manager is not listed as an additional insured, they may not be covered under your policy in the event of an incident on your property, leaving both of you potentially exposed to liability.It can save you money.If your property manager is not added to your insurance policy as an additional insured, they may be forced to purchase their insurance policy to protect themselves.

I plan on being on the road here for work in the next day or two and wanted to try and make sure I have everything covered before I leave.

It is much more helpful than pictures to see you aren't hiding anything.   

Yes you have insurance, but it may not cover everything.