Needs all new cabintry, windows, doors, roof (has some life left), fixtures, fencing, some electrical and plumbing changes, and some framing/drywall due to termite damaged sill plate in areas.

Check out the Life Planner by Lucky Life Tools.  

Fail forward is generally just great life advice. 

Ok, now, conversely with real estate, that is simply not possible. '08' was the biggest hit to real estate in our life times, of EVERYONE alive at the time of it, right.

I am ready to take that next step towards F.I.R.E and set my daughters up for life!

OK, good luck with that if you have easily accessible assets like a home you don't live in.Meanwhile, what are the odds a term life insurance policy pays out? 

Life’s too short.2. you’re making a 5 percent return on total equity now, and surely much more on a return on investment basis.

I already have money left in the property and hesitant on sinking anymore in.  .If there isn't much equity, and there is so much to fix to make it livable, why not do a "deed in lieu" with your lender and move on with life?

I've shifted from trying to economize in everything in life to seeing that oftentimes it's well worth it to pay for the full service experience, no nickel-and-diming.

According to Tom Cruz hereafter referred to as DB, I wasted 31 years of my life training to become an ortho surgeon but the DB doesn't understand some people enjoy their jobs and are passionate about helping other people.