put the new property in a land trust first of all. Second, a lease with option is the way to go. If tenant pays directly to the bank for 12 straight months, he/she may be able to acquire your property via a land contract. This would serve really as a refi, rather than a purchase. That means no realtors have to be involved. The commission being a non factor may make it easier for the buyer to get a lower price, and you, the seller keep more of the proceeds.

If it is in Lincoln Park, near Children's Memorial, has three or more bedrooms and parking...I'll buy it...if the price is right.

If you are unable to sell your current home why don't you try a Lease Option - or rent to buy buyer. Once you have a firm contract with a buyer you can show your lender and they may consider it as an actual sale instead of just a rental. I specialize in "rent to buy" buyers. If you are interested in my program - call 630-219-1757 ext 2 and leave your contact information. I have a condo on Randolph and Canal and have sold property on the Gold Coast and am familiar with the condo sales in Chicago. There is always a way out of a situation if you get creative. You don't make the decision on whether you can do a short sale - you have to qualify with your lender 1st after submitting the proper documentation. I do home retention counseling for one of the top national companies which top lenders use so I am very familiar with this option. Contact me and let's see if we can come up with a solution that will help you out.

Are you certain you will qualify for the new mortgage loan without being able to show a closing date on your current home for sale?

If you don't understand this you need to talk to your mortgage lender and get something in writing that he/she can close without a signed purchase agreement on your current residence.

You don't get to decide if you can short sale or not. The bank must determine if you have financial hardship. If you can buy another house, it will be hard to prove that you have financial hardship. In my opinion, you will be filing for bankruptcy soon. It sounds like you make one bad decision after another. I think the state of Illinois is pretty tough on deadbeats. You should get a lawyer.

It's called Buy 'n Bail! It's today's Fix and Flip!

Some Buy a New Home to Bail on the Old
http://online.wsj.com/public/article_print/SB121314811278463…

Remember, don't get thrown under the bus!

Best advice I could give would be to contact a real estate attorney that is very familiar with short sales. Peter Metrou 630-551-7171