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.

That covered pretty much everything! 

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

By adopting the house-hacking method—living in one unit while renting out the others—we plan for the tenants to cover the mortgage and gain valuable property management experience.

Umbrella Policies are good, but they are not an asset protection tool, they only cover litigation/damages after you’re already in litigation or found personally liable.

The scope of what you asked covers a broad area from estate planning, to tax planning and forward. 

Related damages:When tenant took possession, the living room had a vertical blind set apx 70” long (covering two windows.)