He wants to attempt it again but I want him to understand that with his credit all jacked up the banks are not really working in his favor.The guy wants to use the owner finance as the last option and wants to rent it out now until he knows if the loan modification will go through, I think he is gambling on the wrong thing and will end up losing the house, leaving him nothing but a loss.  

Just seems like such a gamble.   

The parameters are set heavily in their favor to minimize their risk of having to pay out.So you can pay for their services and gamble that you will be that 1 in 1000 customer and come out ahead, or you can do everything on your end to limit your chances of needing their services, and keep the $$ in your own pocket

The only hope for keeping the Portland house is a gamble on equity and rising home prices.

That is why we're so hard-core here about ads, spam, etc.

Also appreciation can be a real gamble from what I've heard.But that raises the question: How does one locate properties that *do* have a shot at cashflow?

Even still, a turn-around project, at its’ very essence, is a calculated gamble for all.

Same rules apply to your first deal as they should to gambling: only risk the amount you can afford to lose.

I used to get hundreds of calls per year from real estate agents who are cold calling using Vulcan7's illegal auto-spam robo-call dialer system.

Of course my accounts are totally personal anecdote but I own over 3500 units on the mainland and grew up here in Hawaii so I tend to have a decent amount of awareness.So going back to the argument that Hawaii will never go down in value... well it could appreciate but I consider that gambling.