I also gambled on very bad section 8 and lost thousands.

Owner offered me 35k with owner financing, however he wants to talk to his renter that rent another property of his that borders the lot I’m interested it.

Now I currently have a job in construction management, and am usually working in the the areas near the NY border and sometimes in Brooklyn.

.$10k/year in negative cash flow verses your appreciation....your gamble and your call.

Goals: -stable cash flow, not as concerned about appreciation (check, assuming description is correct in saying they've had stable tenants. rental price should increase in the next couple years so i have some assurance there)-looking for min $100/unit (check)-C+ neighborhood (check, borders some B/A neighborhoods in upper Ohio City so hoping some absorption goes that way)Other things: -20% CoC return (almost check - Changing purchase price to $53,000 and have tenants also pay water/sewage would bump this deal right up to my criteria of 20% CoC.) 

The building I just purchased is on Lombard bordering Cicero.

Comparatively, a duplex anywhere near Sydney is around $1,000,000 and rents for around $4,000 per month — no possible way to cash flow so you’d be gambling on appreciation.

I am in full agreement that a positive cash flow is a very important goal, due to the fact it insulates you from gambling on appreciation, equity, and rent increases. 

I took the gamble that possible mold remediation in the basement and structural deficiences wouldn't be a greater than $75k issue. 

I can only assume its located in a rapidly appreciating market where investors are willing to suck it up for a couple of years and let price appreciation do the hard work for them (always a risky gamble in any market).