@Will MejiaFor taxes: the first step is to pay an accountant specializing in real estate to estimate your tax hit.

I think connecting that deck down just a step or two to a gravel patio could really expand the feel of the house size. 

I know nothing is easy and there will be challenges along the way but I want to take this step and learn in the process.

I followed your steps and my Pro membership still remains active. 

I guess by “checklist” I meant just the next steps to transition my primary into a rental.

Break it down step by step and you will feel confident to move to the next decision.  

Potential next steps would be for a data provider to emerge similar to AirDNA for medium-term rentals to take on this growing opportunity.

Think of that as a stepping stone to your next step up.  

Meanwhile,  its not unfathomable for the bank who is approving your loans to wonder why this particular borrower feels it's necessary to take such extreme steps to protect themselves...what is it about them or their operation that is leading them to take such extreme measures?

Hey Omri, You are in a good position to take that step in Fix N Flips.