Are you looking into certain investment strategies to begin or certain markets? 

They have solid lease agreements designed to protect you, your income, and your property.Property Maintenance & Repairs: They have a network of vetted, licensed, insured contractors that can respond quickly and do the job right the first time.Minimizing Vacancy & Maximizing Occupancy: Their marketing reduces vacancy time.

I have the option to buy a 1,300-sqft 3-bed, 1.5-bath house in South End neighborhood of Stamford, CT, from a family member before it goes on the market.

And this is so market specific..  

The only money we have going into the market is in our HSA.

There are many markets that this will work great. 

Hey @Paul LaValley welcome to the forums, and phoenix and Tucson are great markets, what makes you interested in those markets specifically?

A frank, hopefully insightful, dive into real estate and financial markets.

Milwaukee Cleveland Toledo great markets.

If the latter, how does that look on a day to day in terms of operating, marketing, and the ownership structure?