First off, i live in Florida and my rental property is in OH.

If Tenant Defaults under this Lease, Landlord may exercise all rights and remedies available under applicable law, including the right to: (i) terminate this Lease; (ii) regain possession of the Property through an eviction or similar process; (iii) recover from Tenant all unpaid Rent, including unpaid Monthly Rent, Additional Rent, Late Fees and, if applicable, holdover Rent for the period prior to Tenant’s delivery of possession of the Property to Landlord; (iv) recover all Rent payable under this Lease for the period from the date of termination for Tenant Default through the stated Expiration Date, less the amount Landlord is able to collect from any replacement tenants for that period; and (v) recover allreasonable costs and expenses incurred by Landlord in repairing any damage to the Property, caused by the improper useby any Occupant or any guests of an Occupant, less any amounts obtained from the Security Deposit.

I have been to the city once and it didn't seem too bad which has piqued my interest in living in the area.

First:  I'm not sure where you live if it would be conducive to this, but you could look into ecotourism and agritourism. 

Not a red flag unless there's a weird pattern like he only sends the most expensive ones.

Duplex, live in 1 side, rent other side out via STR, MTR, or LTR2.

My husband and I own a profitable condo we rent out short to mid-term, while living in a single-family home we plan to convert to a long-term rental.

I've drawn the new build for an owner-occupant to have a single family home but with the option of having a "tenant"/roommate or family member (perhaps in-laws, or elderly parent/grandparent, or a brother/sister, who wants private, separate living space, etc.) living in their own space with their own separate utilities.

My first 2 years with them I lived in Seattle while they managed the properties here in Orlando.

I will live there for a year (It was an REO and I signed an addendum that I have to live there at least a year) while I complete the remodel and then rent the property out to establish cashflow.