I lived in Midwest City for 4 years while serving in the Air Force.

I am still trying to get my first transaction/client, and ultimately my goal is build leverage from my initial deals to generate more leads and more business to make a full transition into running my own RE practice.

Well, attorneys sometimes act like prostitutes.....they assume whatever the client wants.

I agree with @Dan Mackin that COS is a good prospect for long term buy and hold, given the diversity and growth estimates, but I'd suggest Fountain / Security as a starting place for you, not knowing anything beyond the fact that you are serving this great nation (and THANK YOU, sir, for that!). 

How much sense does it make, besides the paternalism argument, that I could invest my client's money in an offering, but not my own?

She still holds parties for her past clients (I need to go to the next one), has a newsletter she sends me, sends Christmas cards, etc.

The paralegal at my title company said that this has been a problem for a client in the past.

I've read about your strong opinions regarding Realtors (I share of those opinions, but I also know that most of my clients will tell you that a great Broker is worth more than anything else in a Real Estate transaction or longterm investment strategy), so I won't suggest that you build a relationship with a Broker who will happily have someone on their team build spreadsheets with the hundreds of names you want.

John Doe serve in the military and met his wife Mary Doe overseas.

I have a prospective client in Sunnyside who hired his handywoman to convert an existing garage to a loft-style studio with a composting toilet.