You are more likely to get a loan mod if its your residence. You can get a loan mod fairlyu easily with a conventional 1st loan if that $2600 is more than 31% of your gross monthly income. The 2nd is another matter. With a short term plan anyway to sell in 3 to 5 years I’d probably sell but its really a personal decision only you can make. I can tell you there is good demand in your area. I just got another short sale approval this morning for a condo in Point Loma so I have seen that demand up close the last few months. The key to a short sale is your lenders. If you want to send me a private message with the names of the lenders I can give you better guidance.