If you're interested in a specific market and you look at enough #'s for enough places you'll know when it's time to pull the trigger.

@Roxanne Rose, a cash-out refi will not trigger any tax event. 

From my research, setting these up seems to be pretty straightforward but following the compliance in terms of managing the funds seems to require some guidance.

LLC: You don't need to honestly pull the trigger on an LLC until you start scaling your portfolio.

Then pull the trigger and allow one of them to list the house.

That said, the bank accepted the appraisal and I remained in compliance of the terms of my commercial loan.

Truth be told, we didn't have analysis paralysis and we just pulled the trigger, for better or worse.

I have a great offer and I was preparing to pull the trigger and execute the assignment. 

I've read a few books on landlording and I can see why it can be daunting to take on, what with needing to be familiar with so many different laws, fielding maintenance calls, potential evictions, addressing non-compliance issues, screening tenants effectively, and so on. 

Know your area and keep analyzing deals-When time comes to pull the trigger you will be able to do it with confident and the seller can feel it.