I can see Cleveland being attractive for better cash-flow and lower barrier of entry, however. 

That is attracting corporations of all sizes to build/grow here, and industry professionals looking to not only buy but rent.

Desirable properties stay rented, are easiest to manage, attract good tenants and decrease your turnover costs, arguably the greatest cash-flow and return killer there is.

Make sure you set it low enough to attract buyers – you may lose some money in the process, but it will sell faster if the price is right.

Hartford is known for its attractive architectural styles and being the Insurance capital of the United States.Percentage of mortgages underwater: 22.4 percentMedian home value: $130,900Hartford not only has a high homeowner vacancy rate at 4.3 percent, which is two and half times the U.S. average, it also has a delinqency rate triple the national average rate.6.

Research successful campaigns and learn what you need to offer to attract investors. 

This attracts lots of people given the price point and proximity to jobs and shopping. 

Or you could just install doors, which would help with draftiness, and be an attractive permanent solution.

You need to think in terms of attracting and how to keep quality tenants,, IE its much like fishing, you need to know what type of bait, where to fish to catch good fish

My intuition is Crowdstreet tends to attract newer accredited investors.