How to advocate for owner financing?

[Jon Sat]

Timing is never 100% ideal... I lived in the same apartment in Chicago for 12 years. Two years ago my wife and I bought a two-flat one block away. We subleased the apartment to a friend and I continue to have a good relationship with the owner. He always said that he’d give me first priority when he sells. Well, he called last week...

The place we bought was a total gut and we’re very close to wrapping that up and getting a renter for the second unit. It has been a slog.

The building with our old apartment would be a wonderful addition to our portfolio and, provided we could up the rent in one of the long-term below-market apartments, it would cash flow and we know the building very well.

I'm hoping to do a cash out refi on the reno in order to get a down payment for the other building (an inelegant BRRR of sorts). Because our DTI isn't as hot as it would be if we had a tenant right now, I'm wondering if the owner would be interested in owner financing.

Does anyone have advice on how I can “sell” that idea to him? I understand that there’s an advantage around capital gains. What else would make it good for him? Is this worth a try?