@Joseph Woodman Lots of factors here, but why not get your feet wet first just to see if landlording suits you? 

Also, the prices I'd seen were so reasonable.. but I've been thinking it might be smart to consider other areas.Im thinking we'd buy and hold forever, and just find a property manager that works for us, mostly because I thought that suited my personality and i like the idea of building a snowball effect of cash flow.

My husband and I bought our first duplex 2 years almost to the day and we have been working to get our next investment property in the near future.In all my research and education, I've realized that I feel stuck in my current day job and I know my skills are much better suited for the real estate industry.

and it’s 2 houses, 1 main and 1 rental / grandmother suite in the back.  

You’ll either drown or learn how to swim.

If further disregard is shown for following the law a suit can be brought against the individual.

Where there is no contract for rent, there is no real chance of a small claims (or a civil suite) awarding you back rent (unless the squatter is really a tenant who is overholding).  

A tennat may choose to break a lease at any time that suites them.

@Gary F.What is the accessory building- garage, shed, gazebo, pool, motherin-law suite, etc. ?

Is the bottom floor like a mother in law suite?