What made the biggest difference in cashflow was creating systems in place with an emphasis on automation.

One of my biggest challenges is that I have not been able to finance the properties with less than 25% down payment and a 6.5% interest rate.

The biggest issue is the law.

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

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.