I thought it would be difficult, but with my background in construction, assessing the repairs needed to the property and the price I needed to secure the contract for was easier than I thought.  

If you live in the property then you get to homestead which reduces an amount from the assessed value, thereby, reducing your tax payment.

You need to assess the viability of renting the property.

You need to really check the % of owner occupied units and the HOA fees and any special assessments that they have or have had recently.  

Financial assistance to friends and family is a-whole-nother ballgame that I do not recommend mingling.At this point, the comments seem to assess that the house needs to be short-saled.

Our 1.3 mil apartment purchase was assessed at 2.1 mil.

In the podcast, he pointed out that a flipper needs to be proficient in several different areas including negotiation, contracts, rehab assessment, appraisal, and marketing.  

Tenant compatibility is even more important as you are sharing common living space.

Additionally, raising rent, shopping around for cheaper, but appropriate insurance as well as potentially protesting your tax assessed value could help.

He bought the house in 1979 for 58,000 according to the county website and the house was assessed for 136,000 then.