For the lease, you'll need to be sure to get one that covers Oklahoma laws. 

To vacate a tenant in a rent control area, requires time and more money..you can read more here: https://hcidla.lacity.org/Is-My-Rental-Unit-Subject-to-the-RSO

If they are all equally qualified (areas covered, knowledge about investing, etc) I'd tell them all that I'd decide with a series of coin flips and I'd tell them that you're doing that to avoid damaging the relationship that you value so much.It's a hard situation, but if you're upfront with everybody, you should minimize the chances of hurting your friends.  

The one year you rented it will be subject to cap gains (in addition to one of depreciation recapture) under the Qualified Use I believe it is called.  

My end goal is to have a passive income stream that will, one day, become big enough to where it can cover my expenses entirely.

Named Perils coverage is called that because the Perils (causes of loss) that are covered are Named in the policy. 

I'm hoping that you could take out a mortgage on the property for $50k for the engineering and if you had to sit on the property, you could at least farm it (or rent it out to a farmer) to make enough to cover the loan payments on $50k while you wait for an upswing. 

There are many good books out there on the subject, but a my personal favorite is one called “The Secret Life o Real Estate and Banking” by Phillip J Anderson.

Your question does not seem to relate to your subject line.

Some of it depends on if you are using cash, using private money, using banks, or using Subject To and Wraps.