We have already talked with multiple HVAC contractors and splitting to two zones is just not an option because of steam heat.

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

I actually had come across your post below in the Events forum and thought to myself it would have been nice to attend that to see first hand a local flip and talk shop about the process.https://www.biggerpockets.com/forums/521/topics/1215682-chec...I am happy to hear that someone with your experience in the region feels that Westchester is a market with some potential.

I get these data through a partner that's a real estate agent so I know what you're talking about.

OR feel free to PM and we can talk. 

You talk to the neighbor and they tell you the city bulldozed the house last week, because it was destroyed in a hurricane. 

That may keep your cashflow the same or even lower it a bit, but you have 4 assets that are appreciating instead of one, 4 mortgages that are getting paid off by the tenant, depreciation and you diversify your risk in 4.Regarding the tax question, you may want to talk to your CPA about that.

Plus, we haven't even talked about the tax deductibles, depreciation, and how the house hack has the potential to off-set your taxes, which is another aspect way of making cashflow (obvioulsy verify with a CPA).

I would love to connect over zoom or a phone call and talk to you about the market and how it's moving right now!

I've found that great things happen when people talk and I'd love for us to stay connected.