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)  

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.   

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

Property Management and Found it.

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 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.  

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.

I am currently living in Colorado and have talked to some property managers down in San Antonio.