Very key thing here, I don't have a finance/economics background, and am just getting started in this area, but this struck me as a good strategy to use.

Since I have no consumer debt and a big beefy emergency fund, I'd buy 3 more single family homes in Alamance County NC to use as LTS in the 300K range. 250K should be enough for 25% down on each plus closing costs.Of course, they'd need to cashflow.

There are always people entering the market and leaving the market all the while the many investors that do this for a living will stay and grab deals.

Here is your mistake, and you are not alone in this. 

I am always trying to learn how to do better in this type of space. 

(I would only do this if the family member has excellent credit and is not in debt themselves. 

thanks in advance;-)

I think the biggest change in me personally and mentally is the realization that you can take control of things and impact your situation more than you think generally or more than the normal person is educated on. 

For an investor you could "drive for dollars" then use the deal calculator on this site to create reports of deals that makes sense in your area.

Quote from @Shawn Benteti: I am an in-progress syndicator.