Real estate continues to be high where I am located and when I calculate the mortgage payment with 20% - 25% down, it only breaks even with the rent I could collect. 

You'd need to make sure the property is in rentable condition and that the rent will be high enough to debt to cover.

The fact is that you have a list of requirements for renting from you, that you present to each applicant and marriage status is not on that list, supports your argument.

I am looking at purchasing a property to live in for a year and then rent.

Plus with larger properties, a few families can split/share the cost to rent.

(Imagine the dog bite, the underage drunk, whatever the worst in you can think of.)I don’t think i’d sign for triple the going rent.

If you buy a package of 6 lesser houses  that means I have 6 roofs, 6 hvac, less cashflow, and likely subpar appreciation(dollar for dollar) compared to better areas.The reduced maintenance costs, higher rents, better tenants, appreciation, and reduced hassle factor for new construction are real and attractive.  

I list on Zillow, primarily communicate with them over Zillow messages and then give our remote login code to enter the home. 2) Maintenance between tenants - This one will be tricky as I will have to transfer all utilities to my name and send multiple vendors to the house for getting the house rent ready.

Not saying all tenants are bad, as most of us just want to make our rent payment on time and live our lives - but don't be surprised if you run into more headaches vs. spending a bit more money up front for peace of mind later on with placing better tenants. 

Regardless, it speaks to him being a high maintenance person I don't want to rent to.