* When do you make owner payments?

I have STR investors in Florida making 25% cash on cash returns, long term rental investors picking up properties directly off the MLS and cash flowing day 1 in various states, and house hackers completely removing their housing payment from the picture allowing them to save for for the next property.The beautiful thing about real estate is there are so many ways to succeed and a plethora of strategies depending on your comfort level and how active you want to be.

What we’ve learned doing lots of off-market negotiation is we get the best results when we have great, empathetic, trust building conversations that gets to the heart of what exactly the seller wants in the transaction besides price.

If it is accrual, then when you actually make the payment does not matter.  

Poor rental payment history is a common cause for non renewal. 

Even if you believe you can stomach the monthly payments, paying $20K a year to carry a piece of land based on the information you shared is not recommended.

In the case of a multi-unit, the units you rent will be considered investment property *I am not a CPA, so trust but verify :)

He took a 401(k) loan to fund the down payment on a four-unit building in a rapidly appreciating neighborhood.

Just call a local real estate attorney , they will draft up a note and deed of trust for you for a fee :)

He has an offshore trust.