However just know that you wont be eligible for most residential loans if you decide to put it under an LLC assuming your needing funding.

These updates modernized the property, improved its curb appeal, and increased its market value.

I come from the mortgage industry as a loan processor and a loan closer and those legal docs templates we used were created by a  real estate attorney, therefore, it's the same principle that allows a TC to do the same thing.

The second property would need to be under a loan product other than a primary conventional.Appreciate it!

All told, there was about $900K in cash and a $1.8 million loan into our deal.

However, I only plan on staying in the property for one or two years before moving to a new home.Do I have to live in the property for the entire loan term (i.e. 30 years), else have my loan revoked?

Do y’all have any recommendations for lenders that offer good loan parameters. 

Would this be in violation of the loan?

That is a lot of negative cash flow.Adding the ADU will have cost and effort but should improve the negative.  

When bringing up subject-to as an option, the agent kept stating that his loan was un-assumable and that there was nothing more outside of traditional financing that could be done.