I'm trying to analyze my first property and not sure how to set it up to run the number using the calculator tools here. 2 of the units are successful Airbnb short term rentals, and the other two units are month to month rentals to existing tenants.

These accountants believe that purchasing from a related party is fine as long as it is an arms- length documented market-consistent transaction.   

Your first couple deals will be important, they will set the stage for your success.

You want to be successful?

I don't see any reason why a legimate, arms-length transaction could not be done.4.

Mistakes and miscommunication cost people money.I did ask him to explain his transaction,  not an uncommon request, but he has failed to answer it."

- FYI: it's only illegal to try to rent it out, the property owner can usually legally live in a nonconforming basement unit.If you do all this you may still negatively cashflow each month, so make sure your income can cover and/or your cash reserves.If you do this successfully, you will learn more in 1-2 years than you would reading here on BP for 5+ years:)Good luck:)

Working with a CPA experienced in real estate transactions is essential here.If I were you, I’d call some attorneys on Monday if this is something you’d like to move quickly on. 

My frind in Omaha ended up picking up his second property sooner than he expected, simply because he’d built a small name for himself with one successful deal already under his belt.Are you feeling confident about the day-to-day responsibilities, or is there something else in the process that’s keeping you up at night?

Success depends on the individual.