Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

My bet is you do not get sued.  

If we face any headwinds, liquid investments go first so probably crypto but then you bet equities will get pressed.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

It isn't impossible but as @Jimmy Lieu mentioned, there is a steep learning curve.Depending on your liquidity, out-of-state buy & hold rentals could be your best bet if NYC investing is out of the picture.

I bet you could make little to no money in 20 hours a week.

I would bet the older homes will see a lot more appreciation than the newer homes, percentage wise. 

If you cannot prove income then our rental DSCR loan will be your best bet. 

Then your best bet are probably community banks which have more flexibility (albeit worse terms) than larger banks and also worth looking into are DSCR lenders.

When you have a duplex and tenants on both sides stay for ten years, it almost guarantees that something isn't right.I would study your market and determine the value of your rental, because I bet you are losing money every month.