Hubris is the path to ruin in the legal field.D) You absolutely need to provide a copy of a demand letter to a lawyer.

I recall one where a women in her 20's, dying of breast cancer, wanted a small dog for comfort. 

You eat well and take your vitamins so you won't have a stroke, heart attack, or cancer.

I let him temporarily stay in the house because he said "he was going through cancer treatment and needed to be close to the hospital and didn't drive."

Is it worth the x number of dollars to ruin my deal?

Look at this way - if you lose the property, or lose so much money that you can't afford to maintain the property, you are ruining the quality of life for the decent people that do stay there.

Absolutely.If you are playing the long game and don't need the cash flow, maximization of resources is less important than reducing risk of ruin or even risk of loss. 

@Ceryn Chen ZIlker/SoCo are extremely popular areas to live or rent, but the purchase price will ruin cash flow returns without a significant down payment. 

You will just ruin your cleaner if you do that every time.  

I saw friends ruined by debt during 2008, so I have played it too safe financially for many years.