From what I understand from your post is that you are a landlord in which you have rented your unit to a company so that they can provide corporate housing to their employees (employee). 

Hoping to get some thoughts on whether my projections are severely off, whether house hacking in NYC would be a good idea at all, or if house hacking in NYC due to the landlord laws would make my investment more of a hassle. 

We buy in Albany and from landlords who think this way and spend a little money and have been able to increase the rents every time.

Hello, I am a landlord of a single family home on the East side.

You can also call the Housing Authority to have your contact information added to their list of available landlords that accept Section 8. 

Would I need regular home owners insurance and land lords insurance for the rental side of the duplex, or just land lords insurance? 

Bay area could support that as most SFR landlords here are high earning techies.  

Would rehabbing and flipping  some of those property with larger land plots be profitable in your view? 

I've made contact with the land owner and they are now asking what we are willing to pay.

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