Third, what is the potential cash flow? 

For your fixer needing conditional coverage post-close:Specialty Insurers: High-risk flexibility.Surplus Line Insurers: Non-standard risks.FAIR Plans: State-mandated option(last resort)

Jacob,Depending on how quickly you will start the fix up, you should be able to insure the Property with a Renovation Builders Risk.  

If so, is it seen as a risk due to localized natural causes?

To explain what I see is a lot of potential investors and investors with limited exposure go down a rabbit hole and spend countless dollars they do not have because someone is trying to sell asset protection to them.  

I wont disagree but you may find that PMI is worth it to get into a specific deal potentially. 

I just want to know if this dream is feasible and if I can potentially get some advice from you all. 

This type of product carries high risk. 

His erratic behavior indicates an increased risk of danger.

And is anything else inside of the trust at risk?