@Melissa Gittens, let me be the think outside the box guy:go to your local place in a dead time of the day, with 4 coffees and a box of doughnuts. go strait for the contractors desk, or the ladies at return desk.... they will take care of you.do this a couple of times, make the contacts.... i have a feeling you may get call backs when deals come to town.....

The roof isn't in dire shape and selling to the tenant has crossed my mind. 

What the bank offered was a strait mortgage loan 5.25% but based upon the rental income of the new property, estimated at $1100/mo based on zillow.

She is pretty much a stranger to you, so I'm not really sure why her poor health and financial straits would have much bearing on taking the best action for yourself. 

I have a line of credit worth around $100,000, abs I would assume that even in dire financial situations 1) my line of credit would still exist albeit pitentially at a higher interest rate and 2) banks would give me a mortgage if I put down 25%.

And finally he would need to be instructed on the importance of not having ZERO savings which places him in dire straights at the loss of only two weeks pay.

Much like @Michael Guydish I've been reading Strait Path to Real Estate Wealth and considering partnering with him.

Can you imagine waking up every morning, knowing that if one thing goes wrong that day, you're in financial dire straights?

If the situation gets dire at the folks house, just rent a house and regroup.  

The book is an easy read with strait forward information, good luck.