You are looking to grow your portfolio to add more income to live on?

I’m Currently living in NY.

Second, an agent no matter whether they intend to make a living at it or not needs to be able to manage their time and schedule.

I am from KC but currently living in Portland. 

It's okay condition for me to live there, but may require some upgrade and some fixing if I rent it out. 

If I were a tenant and my landlord drives by every day unannounced I think I would feel uncomfortable.I understand the need to keep an eye on your property.The tenants also want to be left alone, if you live nearby and walk your dogs and it's your daily route, OK. 

I’m looking to do section 8 rentals in the rust belt, states like West Virginia and Ohio, Although I live in Florida.

There is a much bigger benefit to living in a SFH versus a duplex.

Because I live an hour from there and know the STR regulations. ;)BTW I don't exactly think it's the best area for a STR. 

I live in West Village.