The biggest issue is the law.

House Hacking to help with one of the monthly biggest expense which is rent payment (housing).

Within the last 3 years there has been significant development; new target, top golf, tanger outlets, mgm casino, new shopping center stores, etc. 

However the biggest issue is the location, that neighbor hood is ROUGH, even my "tougher" guys don't like going there. 

I think your biggest mistake was noticing what the managers were doing and either not calling them out or moving on from them.

SteveOkay Steve, here’s the BIGGEST obstacle you have to overcome: you’re uncomfortable with debt.  

Missing documents or the wrong version of the documents is usually the biggest reason for the permit being kicked back. 

I think it is great you are thinking through the situations and risks involved but I believe deals are the biggest thing you need to focus your time on followed by contractor/lender/PM relationships.

My biggest concern is that that with the huge run up in prices in this area, there is going to be a pretty significant correction, and I will be left holding the bag if a correction occurs.I really want to help this family member as they have a young child (4 yrs old) and a spouse who have been displaced from their home. 

Right now, the biggest hurdle I have encountered is how to assess supply and demand for rentals, both long-term and short-term.