@Aaron Zimmerman Good point about structure set up and determining cost bases.

Your first determination is what your tax exposure is. 

Keep learning and determine your long term goals.

I find their platform very user friendly and for those that have no clue about how to pick stocks, funds, ETF's, etc., Wealthfront is a great robo advisor.

Quote from @Mathius Gazi: I picked up a two family last summer in New Haven and it is doing absolutely fantastic.

After having managed in both New Britain and Hartford, I would pick a nice area of New Britain over a Nice area of Hartford - unless you are speaking specifically of the West End of Hartford. 

Would also love to connect with experienced Cleveland rental investors.Much Thanks I see this is a 5-month-old post, how many have you picked up? 

Does the market there pick up more in the spring as other markets do? 

-why not pick a market closer to home? 

I encourage you to interview property managers to determine what their approach looks like when managing properties for an investor who does not reside in the market where the property is located.