The main reason why I created this post is to see the perspective of an investor.

Same applies to any endeavor though from running a business (see the agency problem) to investing in stocks (financial advisors, mutual funds etc.).

We migrated to a more efficient HVAC system as part of the retrofit, but actually ran of the older system during the course of the retrofit.Other similar houses in the neighbourhood have average annual energy consumption 80 - 120% greater than this house.We just acquired another near identical house one block away and I am presently modelling a retrofit plan that, once finished, should see the average annual energy consumption be in the range of 30 - 50kW/m^2.  

May be something you could use just for the houses where you cant see the address from the road to save money.https://itunes.apple.com/us/app/the-driving-for-dollars-app/id1047114587?

If the houses are in a heavy crime block; you will find a motivated seller who wants to get out fast now there are areas like the Hyde Park area where you want to be as that is right in the heart of the new government facility that they start construction on and in time you will see the property  taxes increase which will bring values up and drive the crowd out.

@Alex Hobbs  I don't even see the 60k profit in your scenario.

I see the issue more in the lower end border line credit folks.

I specialize in these areas and see the damage done to out-of-state investors firsthand. 

I included the URLs in the images in case you want to see the charts yourself, but a better option is to load the charts directly using this URL: https://fred.stlouisfed.org/categories/30823The graph above shows what we already know: home process have rebounded for the past 6 years or so since the fallout of the GR (great recession.)

The bonus room conversion seems like the best ROI, but I still don't see the numbers making sense at this price.