Short-term rental loophole and REPS status are the main paths to follow! 

We are about 60 to 90 days out from closing, but we have a gap to bridge between our B to C (Us to Builder) and A to B (Seller to Us) transactions. 

We are thinking of doing Air BnB to rent it out and I have looked at what's out there on Air BnB, HomeAway, FlipKey and other sites to see if similar homes are rented out yet for summer 2018 and it appears they are all still not rented out yet.

My son and I have been the construction side of 6 fix and flips now and have gained the experience and knowledge of hard money and private investors but we are really interested in seller financing. 

But hey we are still hear and enjoy all that we do. 

We are thinking of getting a cost seg study for an SFR that's a short term rental.

We (my wife & I) currently own outright one home which we are renting out.

Our hope is to find ways to increase cashflow with this property short term and reduce our bleeding, and also consider the cost associated to implement.The property is 2 units fully occupied. 1 tenant already rents out our garage for an extra cost, the other tenants are left with no additional storage outside their unit.

Quote from @Zachary Schimenz: I'll keep this short.

We looked into what was required from the owners standpoint and it turned out he needed a slightly different insurance to cover the property's use for short term rental purposes, even though he wasn't the one actually renting it out.