That is unless you have a JV or other equity partner who is putting up the funds immediately with no lien, title insurance, etc.

Absolutely.If a landlord is listed as additional insured (rather than additional interest) they cannot make a claim against one another's liability policy for damages - it could completely jeopardize the coverage they think they're making it easier to get. 

-Will it be robust enough to track additional business expenses that are NOT tied to a single property (IE; Business insurance, Home office, ETC?)

With that they may be able to recoup from their renters insurance (hopefully you require this)  If locks are damaged and the unit isn't secure you would need to take care of that right away.

Plus by going with you, they won't have the benefit of an agent's errors and omissions insurance, the support of their brokerage, and the experience an agent has in protecting their clients from everything that can go wrong in real estate transactions.

.: Quote from @Andrew Steffens: Curious what is the purchase price and taxes/insurance/HOA?

Leave it in your name, get a new insurance policy and call it a day and rent it out

What kind of insurance do you carry? 

The biggest form of energy production in Tennessee today, nuclear power, simply wouldn't exist without many, many trillions in tax dollars to develop, not to mention the government stepping up to insure and protect the plants, manage and protect the waste for half an eternity, and clean up the trillion dollar mess in case of another disaster.

Also you should inquire with insurance agents about the cost to insure.