@Shayan Sameerif you are putting down 20% cash but borrowing 80% from a HELOC, i still think you won't cash flow.i also get nervous when people throw out entire states. 

Purchase price: $15,000 Cash invested: $25,000 Sub to deal - paid the seller and wholesaler $15,000 + $7500 closing costs to assume $84,000 mortgage with a monthly PITI of $575.

If you care just about positive cash flow (and you don't care about population growth, macroeconomics, or appreciation), definitely go with Cleveland.

Are you cash flowing the property?

Getting a property with a 3% mortgage that offered both equity appreciation and solid cash flow is what sparked my passion for real estate investing.

Buuuuuut, I'm kinda proving the point in being upfront with my bias aren't I. 

I'm terrified of doing all this research, finding a "dream" property, only for it to fail and negative cash flow. 

When interviewing property managers, make sure you ask plenty of questions, thoroughly review their management contract, and request references.A little due diligence upfront can save you a lot of headaches down the road.

Are there any other markets that really pop and stand out for cash-flow and easy entrance? 

If your goal is day-one cash flow, the current high interest rates will make it very difficult.