Would you say your perception may be different from most people because of your accountant background?

With your background in lease management and site selection, that could be a natural next step.Regarding STRs, I can understand the hesitation—accurate expense tracking is critical, and not having that data can make evaluating deals frustrating.

However, a simple security system would deter this.Personal Safety -  I assume you are using their ID to run a background check and deciding if their history affects your safety, correct?

You have the means to purchase and intend to offer owner financing (you) to the buyers of your lots.That sounds pretty straight forward as long as you are able to carry the loans and deal with any defaults.I don't have a background in raw land deals, so that's all I got.Thanks for the feedback and I will keep these things in mind as I move forward. 

Quote from @Dominic Mazzarella: Quote from @Sean Barnebey: This is an interesting opportunity, and it sounds like you’re approaching it wisely by considering the numbers carefully.

I have a personal CPA, but they don't have much real estate background. 

My education background is in computer science, mathematics and some corporate finance, as well as have some internship experience in the quantitative finance space.

Vrbo is your suit. 4 bookings out of a whole year are nothing compared to the advantage you get by dominating the market on a platform.  

Coming from a health care background and Not having any previous experience in Real Estate or sales, I am having trouble getting the Bio started.  

With your background in the Air Force, MBA, and construction, you're in a great position to launch a real estate venture.