It sounds like you are getting too soft maybe with rent payments.

We first reached out to originators for Freddie and Fannie and were told that the deal looked great and we should be able to get the following terms:-Non recourse loan, 80% ltv-30 year amortization-10 year fixed rate-4.25-4.5% interest rate-Interest only payments for the first two yearsFreddie has since come back and passed on the deal due to our market being too small and the age of the property (1984).

nope, these two actually have the documented ability to make the payments at a reasonable debt-to-income ratio.I'm coming up with ballpark $345k/mo PITI (my homeowner's insurance assumption might not be accurate, I didn't pull the actual property tax bill, and I don't know if there is an HOA so I left it at $0).

She was never late, but the mortgage payment was high for her, so she has now done a modification using the FHA-HAMP program to lower the mortgage payment while she is ramping up income (having been a stay at home mom for the last 15 years).  

This was effectively a 6% risk free interest rate arbitrage thats been running for close to five years now.now I'm in graduate school and get them at 6% (interest accrues immediately), I've used it for remodels and down payments. when your done with school, you can opt for the balance to convert to a 30-year Amort.

How much money will you need to make an offer on a Fix and Flip that will be funded by Hard Money and Gap Funding?

From what me and the borrower agreed, the payment in full is due within 6 weeks of borrowing the money.

We recently cashed out of a Brooklyn condo, and the equity would go way farther as a couple of down payments in better value markets.  

She told me in private that she bought the house with a low down payment of a "couple of thousand" and that she put in her pocket $140k.

Here's an example of a mortgage and Cash Flow analysis results.  20% Down payment =  $9,600, Loan amount = $38,400,  4% APR/30 years,  $183 monthly payment