At the same started doing small deals (duplex, triplex, 6 units, etc where I could execute a heavy rehab / value add play).2012: Bought my first bigger deal at 35 units with one $$ money partner already in my network.2014: Syndicated a 60 unit deal and never looked back.

Most rental properties owners/lanlords intend to sell sometime before they die- so time does play into the irs intention for LTGs. 

You're losing money each month before you even factor in Vacancy, Repairs, CapEx, or Management.It's one thing to make an appreciation play when you have 20 years experience and a few hundred cash-flowing doors under your belt.

DTI will come into play.

I used to find myself playing little games like "well, if I can lower the interest rate by 0.5%, this property would be in the black monthly".

Doesn't debt to income come into play with refinancing?

@Jorge RiveraI think the best play is a 2 bedroom you can convert into a 3 bedroom.  

Nothing was flowing into my head until the Billy Holiday song "God Bless The Child" started to play in the background.   

The fact that they led you to believe you were a "1099 employee" (again, no such thing is to be found in the tax code) leads me to suspect that they know damned well they're playing fast and loose with the rules. https://www.irs.gov/businesses/small-businesses-self-employed/independent-contractor-defined

Unless it’s a flip, value added play or a refinance that was purchased years ago during the recession.