I am an investor/agent and own 5 and it's my primary investment strategy.

That means either you won't cash flow or your Return on Equity (ROE) will be terrible.Since this is your primary residence you'll be exempted from paying capital gains taxes when you sell.If you sell to your parents, it will be considered a non-arms length transaction and will get closer scrutiny.

My wife and I are officially under contract with a new primary residence, with the goal of moving and then turning our current home into a rental.

I would have bought rental properties of any sort before I bought my primary home. 

I'd highly recommend getting a primary residence first or house hacking. 

Did your primary become rent controlled and if not what exempted it from rent control?  

Hey Ed - this one wouldn't qualify with DSCR if one of the houses is your primary (assuming all are on the same tax parcel).

Thanks, Collin for the detailed explanation.

What these $20 - 40k “mentorship’s” sell is a SHORTCUT, but it does NOT work because the PRIMARY real estate education and knowledge MUST be there in order to be able to implement and strategy or tactic correctly, at the correct time, and under the correct conditions.  

Hey,If "building class designation" is the same as zoning, then this seems like it can definitely be appraised as a two family, with both the legal and actual designation as a two family.Depending where in NYC, that may not help your valuation, as primary residences sometimes sell for more than investment properties, so check that out before challenging the appraisal and definitely before paying for another one.Double check all this with your lender/broker as well.Best of luck!