Any one of us could give you our two cents on the math of it, but only you can decide if it makes sense based on what your specific goals are. personally, i paid points on my house because my goal was lowest possible monthly payment.

Mortgage payment is approx $1800.

I did my research and requote what would benefit both me and the investor, below is the Finalized CORRECT format of the proposal:Listed price on the property: 459,900MAXIMUM amout of money down on the property: $380,000Method of Payment: CASH OFFER from Investor.

Know that every long term lender will require a survey and if something comes up on it when you are trying to sell or refi, you could get stuck in hard money without an easy or quick way to get out.Is there a pre-payment penalty?

Add-on:  I do like that I can automate my late fees, no partial payments, etc.

And of course, if your actual cash value is less than the current mortgage(s) on the property, all of the cash value payment will go to the lenders. 

It can take 2-3 months before payments get approved. 

This is the equivalent of a car salesman pitching the "monthly payment" of a car instead of the actual price of the car.

You should find out what percentage of the rent is being paid by S8 and by the tenant.Tenants have to sign the rent increase and some won't because they don't want their payment portion increasing.It's also highly unlikely a S8 office will approve the huge increase from $797 to $1300.- BTW: the $1300 includes all utilities being paid by the landlord.

Since you'll be owner-occupying, take advantage of low down payment loans like FHA (3.5%), Conventional (5%), VA (0%), or a 203k loan for renovations.