It's good practice in making the calculations needed to decide whether or not to pull the trigger on a potential deal.You soon learn that starting off as a Doctor is less advantageous than starting off as a Janitor, because the game presets your income and expenses based on the job title.

And after a year or two you can move into it and make it your retirement home without triggering the tax. 

I’m currently looking into the best ways to structure guest payment flows to ensure legal compliance (that may restrict non-licensed property managers from collecting rent directly) and seamless operations.

Almost none of them ever pull the trigger.  

That will dramatically change the nature of the wholesaling business with the legal compliance factor that agents need to comply with.

If that's the case I would strongly suggest building your team before pulling the trigger on an Airbnb.

If you did the refi 3 months after, it could trigger them to audit you.

You gat pull the trigger.

Therefore, transferring our jointly owned investment property into my SMLLC would not trigger a due-on-sale clause?

I’ve heard different things like taking a Fannie Mae loan out then converting it to a LLC and the likelihood of triggering a due on sale clause is minimal.