I'm more concerned with a liability claim from an auto accident than from a rental property. 

But could i ask for advice, suggestions, questions i should ask or concerns i should have from all of the much more advanced members of the forum?

As a listing agent that is a top concern when we pick one of muntiple offers.

But I'm concerned because you use the word "gain" of $250K. 

My point of concern is in Capex.  

What I always tell people is that somewhere there is a little girl who could be the next Albert Einstein, but without our help she is more concerned with where her next meal is coming from or if she will have a roof over her head to be able to focus on life's mysteries.

My biggest concern, however, is how that payment impacts my DTI and ability to get lending going forward. 

Would probably involve putting in a permanent foundation, and re-siding the home at least (probably getting a permit for a remodel) - not an inexpensive proposition. 

The question is, do you as an owner want to get the work done properly, quickly quickly, and efficiently, or are you more concerned with an itemized invoice?

It's truly a life hack, so we're not ready to settle down into a permanent home just yet.