Haven't fully jumped in yet and the concern is that without a job it would be hard to qualify for conventional financing.

The 2 daughters are on board with selling, but concerned that the government, Medicare, etc. will 'take' the proceeds to pay for his care. 

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

Spend some time - find some mentors - buy a few coffees and get really comfortable that you know all of the hidden dangers to the investment you want to make and then, pull the trigger.  

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.