Shoot me a message if you want to talk further.

There are a few things to watch for: if you are a nurse and work night shifts and your tenant has kids that make some noise, it may not be a good situation. 

If he is a contractor, why not buy the house personally and pay him a fee for his services.If hes a realtor, why not just pay him a commission to buy the house.Best of luck

...and don't forget to collect a W9 right away and a copy of their insurance!

I'd start with a small fine for the first offense.

I tried to research the best and most user-friendly PM site that did not charge a fee to maintain a property, being that it was my first one and I was self-managing and not using a PM.  

Windows are often also a point of contention. 

It is the perfect home for me (as an airbnb) but it's undesirable to a regular person since it's dated (its a late 1960's home).

I've worked with this lender several times before, but always on single family new construction.I'm building 2 town homes under a single roof, on a single parcel of land. 

It is great that you are already thinking ahead about scaling your portfolio.Since you are a veteran, have you looked into using a VA loan for a multifamily property?