A couple strategies that could make sense for a younger person without experience could be a live-in flip or a house hack.

Providing for the disposition of certain personal property following an eviction.

The concept of "EARN" is gone in these hearts and minds.

I've personally driven this neighborhood and was amazed at how nice and clean it is.

Little did I know it would take decades to ripen :)3. bought a foreclosure sale .. traded the house for the 3 acres the person who owned the house. 

Id have a lawyer on hand, this person seems like they will escalate issues once you notify them you aren't renewing their lease.  

For instance, said property manager manages maintenance issues, problems that arise during bookings, basically anything that needs a physical person at the property, while I manage the rest?

No Personal Use: You or family members cannot live in or personally use the property.2.

Not sure if they have upgraded to desktop appraisals but if they are still doing in person appraisals , make sure you get everything (scope of work, good faith deposit, social, LLC docs, insurance, proof of prior experience, financial statements) in ASAP.

I am here to create a business strategy that protects personal and business investments and mitigates risk,  procure a coach or mentor, and set up tax strategies to create long-term wealth for myself and my family.