Of course, it is entirely possible I am suffering from Shiny Object Syndrome and need to be slapped in the face.

I live in Los Angeles so I must be suffering from the "there must be something bigger and better around the corner-itis" 

I completely agree with @Thomas S.Of course it breaks our hearts to see people suffer.

You could prolong your financial suffering and continue to supplement his rent but your best option would be to go directly to $1550 and stop losing money.

Plus the appreciation really suffers if you do that. 

The city plants a tree and grass in the curb strip/berm near your property.

Current value $80,000 to $90,000.The buyer: A close family friend of the seller. 30 year old blue collar worker that suffered a health issue costing him his job and resulting in a foreclosure on his house.

The property is not currently on the market but I'm very interested in planting the seed to see if there's any interest in selling.

Part of getting into REI is so that we can spend more of our time together rather than spending more than half our day at other jobs and commuting, getting to work together is a big part of why we want to take this on (and the potential that RE Investing has for financial freedom).My Concerns: I originally thought I would develop myself as a contractor and do most of the work myself at first, but when I consider the time constraints (holding a house way longer to do the work myself, and the quality of work suffering) I realize this isn't an optimal plan.

Same with the sewage plant.