But your cash flow suffers and there is the potential for negative cash flow because rents don't hit the 1% of purchase price mark.Cash Flow Markets - the midwest. 

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. 

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.

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.

I’d rather suffer the depreciation  with a condo than that of a SFH.

I enjoy what I do, but realize that I may be suffering from compassion fatigue, and so I am seeking other means to put food on the table.