So, that’s a plus that I’m not a complete stranger but none the less still a stranger (I’ve never met the owner but met his property manager when I was home for Christmas last year)  

I own BlueRibbonHomes, a full-service brokerage that includes property management.

The full guidelines on the Freddie site for LLC are:Permitted Transfers of Ownership subject to conditionsIn situations where all of the following conditions are met, Freddie Mac will permit a Transfer of Ownership of the Mortgaged Premises:-At least 12 months have passed since the Origination Date-The Servicer has complied with all mortgage insurance requirements applicable to the transfer-The transfer is to a limited liability company (LLC) or limited partnership (LP), provided that:The managing member/general partner of the LLC/LP is the original Borrower.

This would include your agent, property manager,  and contractor.   

Property Management and Found it.

The owner owns it free and clear and it's managed by a local property manager.

If you find a property, call a PM and tell them you have a property and you'd like to talk with them about managing it - ask about how they handle tenants/evicitons/screening/ and most importantly do they cover the area your property is in.... if the answer is NO then RUN AWAY.  

Before making any decisions, review the information provided by San Francisco's Office of Short-Term Rentals website, consult with local experts such as real estate agents or property management companies that specialize in STR.

If it's only 2 properties and I manage them.

@Nathaniel LinnIn order to invest in real estate, start connecting with local agents, property managers and lenders in Ohio.