I have clients who want to attempt a short sale on their rental property. They paid about $600k and now it is worth $400k, after their rental income, they still owe $1,200 each month to cover the mortgage. Their mortgage will jump up this summer so they will be in the hole closer to $2,000/month. The problem is they are doing fine financially, it's just draining their funds and not a good investment.  What is the best way to position the situation to the bank to hopefully gain short sale approval?  Any thoughts on dealing with rental property short sales? Two lenders, too!

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Stephanie,

The lender(s) may still approve a short sale, regardless of their financial situation. But, they should be prepared to sign a promissory note at closing.
I'd give it a shot Stephanie. I'd position it as a "strategic default" where the owners have just made the business decision to walk away. The second lien in this case actually helps as they ought to be fairly motivated to take a discount vs. get nothing. That leaves more net to give to the first (close to a full payoff would almost make it a slam dunk).

Then you need to start prepping the sellers for the possibility of the lien holders asking for a contribution via cash or note. As long as the contribution was small enough that they were still much better off financially, it would be a simple business decision.

Some people focus on the moral hazard guilt issue on what is going to be a much more prevalent scenario; but, I focus on helping people the best I know how and not on judging them. It's the old - "people in glass houses" thing with me! ;-)
They do have a hardship! Their money is being drained by the negative payments and soon they will be out of money. Sell the bank on that part. But they do need to know that the second is going to want a note or cash contribution which you need to prepare the seller for. This is a business decision for the bank and the sellers. Fight for your sellers!
Thank-you so much for all of your comments! I really appreciate your help. I will see what we can do in trying to plead a hardship from loss of money long-term. What is a realistic amount the bank might ask for in a note?

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