@Ko KashiwagiYes, without the Triplex' mortgage, or if at least a portion of its rental income can be counted against the payments, my DTI would allow me to qualify for the amount I intend to borrow for the new primary.

Hi Tomas,DSCR would be a great option considering they are based primarily off of the property not the borrower.

When using the Fannie/Freddie/Federal Home Loan Bank second home occupancy loan and you transfer title within the first year to an LLC that the borrower is majority owner of it will not trigger the due on sale clause as long as you can attest that it will continue to be a second home.  

I am not a lawyer but generally the life tenant cannot sell or borrow against a life estate without the remainderman's permision.

Does a member having orders allows a borrower different options? 

They certainly would be ok with you going to another bank and borrowing $450k.

Depending on the lender for a DSCR rental property loan, rates will be about 0.125% to .25% lower if you put 25% versus 20% down on an investment property purchase if it's the same borrower credit score and profile being analyzed. 

It's advisable to work with a real estate attorney who is familiar with subject-to transactions to navigate any legal complexities.Risk and Liability: As the original borrower, you retain liability for the mortgage even after selling the property "subject to."

I was contacted by the borrower directly.

But imagine you don't pay cash but rather borrow so your 5k cash/closing-down payment to buy a 100k STR, then in year 1 it rises 2k - only a paltry 2%, but you make a 40% profit as you are levered 20:1, and that beats the best year for stocks ever.