While I am neither a big fan of our federal government or how my social security money is invested...I would like to raise a few counter points- SS also has disability components to it- SS was never meant to be your only retirement plan, it was meant to provide a base and be part of three prong approach of SS, pension and 401k/individual savings- SS was meant to provide base level of income The bigger problem for me is companies have removed pensions and lowered 401k contributions while life expectancies have greatly increased making SS possibly insolvent in the near future.  

However, with the quoted rate often being an average, what are your favorite resources to delve deeper into the components of the average? 

That would be a specific scenario however and not the general fact pattern.Appreciation and/or loan amortization are probably the components that are flipping ROI positive if cash flow is negative and holistic ROI is positive.

And with 4BR/2B and a partially finished basement, I'd be able to rent out at least one if not two rooms to help keep my costs down and start getting landlord experience.My realtor pulled comps, defined as all 4BR/2B properties on less than .5 acres (subject property is .31 acres) in the last 6 months in the zip code.

Most of the chronically homeless on the streets around here - despite rhetoric - aren't people who have been forced out of their long term homes/apartments by rising rents - they are drug addicted or mentally ill people who cannot hold a job, a criminal component, and some that prefer the lifestyle.   

Real Estate in general has a very high turnover but Property Management adds an extra component of brutality to the game.

You should define multiple exit strategies for your flip.

The difference here is how the insurance companies define coverage.

Land is defined as everything not supplied by human effort.

It helps to define a measurable success or a miss.