I am glad you highlighted the management piece as this is a crucial part of buying in another market.Excited that you are stabilized and are generating cash flow on that deal. 

There was a great feed the other day with about 35 awful pieces of advice which mostly noted: "quit claim deed the property"...

Everyone want a piece of the pie.Joe Gore

Wishing I had bought a duplex or really any piece of property straight out of high school for a jump start but here I stand. 

One piece of advice I took from Brandon Turner is do one thing each day to move the needle forward. 

He casually told me he sends out 10,000 pieces of mail every month. . .ten thousand!

Although I am just starting my journey, (just recently sold first piece of land; acquired in 2016–held and sold this past week) I live in Southern California but looking to expand to Florida and other states for REI. 

. - I was in a VERY similar situation here in Chicago, but I had less experience working on my own than you.I had a piece of land that I owned free and clear, but since I didn't have any development experience, most of the banks wouldn't talk to me. 

Quote from @Brian Christinakis: Let's not forget the liability piece that STR insurance provides in MUCH higher liability limits for incidents ON your property but also incidents off your property while your guests are staying there (like using a bike).

Finding borrowers won't be an issue, so I wouldn't worry about that piece, just making sure you have an agreement you are comfortable with and borrowers and properties you are comfortable with.