Have the correct insurance to cover STR activity in your home (Proper and CBIZ are the two major players in that area) AND have an umbrella policy in place.  

He owns a used car sales business, so what does he profit each year?

But, I am severely a rookie and am going through some major analysis paralysis. 

Schedule C on your taxes is titled "profit & loss for business" so with your STR income now being labeled as a business, (because it is) lenders will want to see consistency and growth in order to be able to use any of the income to offset the STR's debt services.  

Those rules can be changed at any time if the majority of owners agree to the change.

A major dip in the home owner market can and often does wipe out a large portion of equity. 

I am reconsidering if I should hold the flip under the C-Corp or perhaps create a NEW LLC or S-CORP, take out a SBA Loan, fund the house, and pay back the loan immediately and have access to the profits for a future flip or to re-invest. 

At the same time as this was happening, I was actually in the process of changing majors in college (I'm a junior at JMU in Virginia,) and had dropped a few courses, so I felt I had some time to commit to the endeavor until my next semester starts.

Both 3 unit houses cash flowed right out the gates and will continue to profit greater as I improve the places and raise the rents.

Can carve out responsibility and control of profit loss and agreement for common expenses within existing LLC.