I feel almost sick admitting it, but the truth is I think I love short sale transactions (working on the listing side of course.) They're a challenge, they're a lot of work and time, but I get them and I understand them now and ...of course there is always a level of risk that they won't close YET I still enjoy working with a short sale. I love the partnership I have working with the sellers on their short sale, and I love the efforts they place into helping me sell their home. This is not easy work for anybody!
After thoroughly screening the seller to understand as clear of a picture as I can, I make my decision on whether or not I should list the property.
By experience, and I've been burnt before, it's important to say "no" when I see that:
1. Either the seller is not capable of handling such a complicated and draining transaction or
2. The position of the loan is such that it will foreclose before I am able to sell it or
3. The primary and secondary loans are held with lenders who are uncooperative from the start
Though I haven't had the experience of working with many higher end short sale properties, I've certainly seen quite a few of the properties below $200K who were great candidates for short sales.
The key is to not fear the bank and to know what you're after before making contact with the seller and their bank each step of the way. It's also important to be open and honest up front with the seller and the bank. I always keep in touch with the bank, let them in on showing feedback received and do regular price reductions until the fish begin to BITE!