We are very much alike, so everything you said there resonates with me.

This is quite a common scenario but not knowing some more intricate details of your situation, I would recommend for you to proceed with a sale as the your monthly rent would not be sustainable to cover your mortgage and repairs/maintenance as well as management fees.

When you find someone who resonates with you and your learning style, you might dig in deeper to see if they have more material on that subject. 

Now your high level theming has to really resonate with people.  

Meaning your R.E. boom is NOT standing on internally sustainable metrics, it was via foreign (out state) dollars flooding in.

The reason I bring this topic up is because I am looking at approaching an owner about buying his 3 family that sustained significant fire damage.

Not knowing, what his professional or employment prospects will be as he gets older, I want to build a business that generates a high volume of cash flow to not only provide my family financial freedom in the near term, but to build a business that can sustain and fund his life in the long run.

Coverage limits across all locationsCoverageLIMITSDEDUCTIBLEProperty Deductible---$1,000Building Glass Deductible---$250Business IncomeActual Loss Sustained for 12 consecutive months---Employee Dishonesty and Forgery$25,000$1,000General Liability$1,000,000EACH OCCURRENCE$2,000,000GENERAL AGGREGATE$2,000,000PRODUCTS & COMPLETED OPERATIONS AGGREGATECoverageLIMITSMedical Expenses$5,000Damage to Premises Rented to You$300,000Other CoverageCoverageLIMITSHired Auto LiabilityIncludedNon-Owned Auto LiabilityIncludedAdditional InsuredAdd or Manage

I don't know enough to know how sustainable that is at current rates but know damn sure that it makes the 1970s and the rest of the interest rate trend chart meaningless from a "normal" standpoint.I think it's very clear what the Fed is doing and will keep doing. 

The market is not sustainable appreciating at 30% a year.