What I see is typically in the $3k - $6k range for those types of properties.

It's best to reach out to multiple lenders to explore your options.

The $380K insurance payout is typically not taxable if used to restore the property.

@German Fernandez Love those options!

As already mentioned, he wouldn't be able to use rent from roommates to help qualify but based on the numbers you shared there should be a VA option available considering how much flexibility there is. 

@Cole Starin sometimes it makes sense to sell the WORST property in your portfolio.Another option is why do a LOC on the duplex, when you could just do a $100k cashout refi to pay off all your debt AND keep the property?

FHA loans typically require the property to be a primary residence for at least one year, so he should confirm compliance with his lender.Once rented, he can deduct expenses like mortgage interest, property taxes, maintenance, and depreciation starting from the date it's available for rent.

Also, I am considering alternative financing options (beyond Hard Money).

I typically focus on off-market deals, so I didn’t work with an agent to find this property.

Being a NYC resident (originally from Long Island), the price of entry in the area is on the higher end, so I've been considering some options in the NY Capitol region, as well as NJ and CT.