Drive the city looking for dumpsters in yards.

I was born and raised for about 10 years just outside of Charm City. 

*Side note some policies may offer "Repair Cost" settlement which is a nice option that falls in the middle of RCV and ACV and may not require you to insure the dwelling at the full replacement cost estimate.For those outside the major Ohio cities you may have a small stroke hearing someone say to insure it for less than the full RCV.

My biggest concern is not having enough of a safety net for that second purchase. 

Since you’re already on BP, when you find a target market I would repost this question rephrased as “can anyone out there investing in city X recommend a great agent for an oos investor.”

@Joshua Feit my biggest tip would be to make sure all of your numbers work assuming you long term rent it i.e. don't rely only on STR revenue in your analysis. 

LAS COLINAS ASSOCIATION, IRVING CITY, DALLAS COUNTY, TEXAS. 

It is not a city in which undertaking a first project at scale would be advisable.

FYI - if it helps - I'm based in the Chicagoland area - just about 20 miles outside of the city.

So I've been strategizing how to start my RE profile in the next year or so, but the biggest things is saving to get that 10-20% down..