This whole thread was like a car accident....I just couldn't stop looking

You have to run numbers and then jump in or run away.Also realize that you never stop learning. 

In 2012 we moved back into our Evans, GA house and lived there as our primary residence until 2015 when we moved into our larger "long term" home as we decided Evans would be our final stop after retirement. 

Apply the same effort you did to baseball and no one will be able to stop you.  

If they let you go on leaving your wheelie bins out for 3 days, leaving construction debris on your lot, letting your grass grow or parking unregistered cars (all violations in our HOA) and then I come along and add a garage to my property that encroaches on the property line (but still within city code-this is Colorado now) and the HOA tries to stop me they may well be SOL.

Hope you can stop by. https://www.biggerpockets.com/forums/521/topics/54...

(Are some self directed plans different from others)2-If so, how much of the money borrowed would I be required to place back into the fund? 

In any case, I don't recommend deliberately borrowing more than 70% of your home's value.

Best thing for stopping this problem permanently is removing the tree (aesthetics and city laws notwithstanding). 

If borrower is current a short sale may or may not be an option depending on investor guidelines and if borrower is facing imminent default on the mortgage.