The dumbest questions are the ones you don't ask, and just absorb the loss instead.Lots of people here have been right where you're standing.

@Brandon Leong my experience when getting insurance is my insurance broker tells me what the coverage is based on several factors that I give to get a quote (I've gotten quotes for SFR and quads):1-how far from fire hydrant and fire station (she figures this out for herself since I give her the address)2-roof age and here in Florida, wind mitigation3-age of property4-is it in a flood zone5-she does a minimum mandatory coverage amount and then I tell her how much more in $$$ I want covered. this is based on how much will it cost to rebuild.6-the rental loss is included so I don't need to ask about that - at least for me it is, not sure if others have to ask for it to be included.7-what type of electrical and plumbing are in the house if it's an older home.Perhaps talk to a insurance broker and tell them what you have and ask them for a quote.

Make sure the system is property sized according to fixture units, velocity ,and friction losses.  

Does anyone have real experience owning and operating multi-family rentals in Brooklyn and is willing to shed some light on the market and provide some pointers on how an inexperienced investor like myself doesn't find himself at a loss? 

Recovery of your investment in the rehab would typically be through the sale of the property and split of the profit (or loss).

You make your money when you buy...you realize your profit when you exercise your exit strategy down the road.If you do anything now, rationalizing on future events you have no control over, that will recover your loss (overpay) at purchase, you lose.  

Does anyone have an MS Excel model for Property Development Feasibility Studies?

I have a full-time job and my initial reason for acquiring a multi-unit property was in order to live for free aka house hack and, more importantly, to write off the expenses (renos, mortgage, etc) in order to get more taxes back at the end of the year.When "pitching" a portfolio lender, does it hurt you if you have been breaking even or reporting a loss for the above stated purposes? 

I know the general feeling on the forums is either (1) fire him / cut your losses or (2) suck it up and move forward as some of it is my mistake for not insisting on receiving the plan (god knows if they're even following a construction plan). 

Is this a feasible way to get a deal?