Nickerson added “exchanging” real estate to upgrade to larger holdings without paying capital gains tax to his formula, and a number of other books were written about the subject in the next 10 years.  

Buy BP's books on creative financing, zero down, subject to,  pre-forclosure, even short sales.   

So either way you do it you will be subject to those costs and for the first years majority of your payment will be applied towards principal. 

This is a subjective question, and everyone will have a different answer to the same area.

Appreciate any knowledge and advice on this subject!

BACKGROUND: Bought a property SUBJECT 2 an existing 1st lien (lets say serviced by Shellpoint) years ago.

However, not everyone has the income to qualify conventional, so the alternative route would be DSCR loan where the program doesn't look into your income, instead it evaluates based on the subject property rental performance based on the ratio system.

Stuart you bring up a point that reflects a whole subject that’s a topic onto itself.  

For a subject-to (subto) property you plan to use as a short-term rental (STR), you should provide the lender with a regular home insurance policy to meet their requirements.

All of the risks of "subject to" then come into play (with a "wrap"); read this thread:http://www.biggerpockets.com/forums/83/topics/86029-subject-2-protection-from-calling-mortgage-due