Most importantly, the property backs to a city greenbelt and homeless people will camp out there and scare the daylights out of my tenants.

I know he’s just trying to scare me, but it’s working.

Cashflow may not be immediate but if you run your #s, you'll be able to see how long it'll take to cashflow and what kind of equity you can expect to build within your first few years of house-hacking.I began househacking in 2010 while working an NYC job (Health + Hospitals Corp., formerly HHC) earning a base salary and overtime pay that are nearly identical to what you posted here.

That is a health code violation.

I am not so scared of the market that I think I can't beat that with real estate OR stocks. 

It has caused problems not just with housing, but health care.

If you don't have the additional mental bandwidth, can't deal with stress in healthful way or do not have much time to commit atleast 14 months of focus then do not build.

I have also looked through my files of non-buys: scared off on inspection, fell apart in negotiations, numbers didn't quite crunch. 

The challenge for many of us seeking to replace our W2 income is coming into it with a serious financial deficit: bad or no credit, little or no savings (left after the crash, unemployment, divorce, health issues, etc. or any combination there of), sparse personal network, ...

I could have found the money I bet, but I was scared to be a landlord.