Workout a deal or wait until larger down payment saved?

[Cyrus Hanson]

I've been knowing a gentleman for around 3 years who owns about 40-50 houses in the area I'd like to purchase another duplex or triplex in. We are casual friends and chat about cars every few months or so via text. I briefly brought up the idea of him selling a house to me and he mentioned he had just sold one to a friend, so I know there is a possibility he'd let one go. 

I closed on my second multi-unit this past February and am still building up my savings to position myself for a third property, so I don't quite have the down payment needed to finance one of his houses conventionally. I didn't think of approaching him prior to buying my second property, but c'est la vie.

There are two possible options in my head:

One: Approach him about providing owner financing for one of the properties and work out a deal if we can make the numbers work. I know quite a few of them are owned by him free and clear. One reservation I have about this option is the risk of not appearing serious because I don't have a large enough amount of money to bring to the table quite yet. Also, if I approach him too soon I might ruin a future opportunity when I have more money to work out a deal with a higher chance of completion due to bringing more cash to the deal. 

Two: Wait until I have enough money saved then approach him with an owner financing inquiry or conventional financing for one of his properties. The risk here is him selling one of the properties to another friend instead of me, and me missing out on a deal. Also, maybe he simply won't want to sell later but is OK with the idea of selling sooner. 

I am leaning towards just creating a possible owner financed package to present to him in the short term with the amount of money I can afford to put down.

Please let me know your thoughts and ideas on this and if you know of another option here I am not seeing. 

Thanks!

Cyrus