The Menger Creek linear park 7.4 million dollar project, Dignowity is booming and about to be deemed historical.

You didn't mention any future rent increases.

I'm not trying to get in over my head on a project that will require more then I have to give (in time and knowledge), however my job does provide me some flexibility.

That election is binding unless you later revoke it and covers all future purchases.

We focus on updating the old and neglected housing stock across multiple Midwest markets where we can get in and out of a project within 2-4 months, and often complete a project for a rehab budget that is less than permit fees alone would potentially cost in CA.

Real estate has been my best investment, but it has only outperformed index funds due to taking on heavy rehab projects and leverage (which looks great on a spreadsheet but is really nervy in real life). 

Assuming RentingFamilyMember continues to file Schedule E, would/how does that affect the real estate capital gains exemption on a future sale?

It is stored for future use. 

The earlier you start in your RE journey, the better off you will be in the future.

I would like to visit these cities again in the future, and I plan to.