If he wanted to stay, he could stop paying on the 2nd and there is very little liklihood of CW foreclosing on him. He may want to consider that as an initial strategy. If he wants to do a short sale, he needs to be able to document a hardship which isnt all that tough to do. An experienced short sale agent will guide him through preparation of the short sale package. He will need to get CW to agree to it and the 1st TD holder will probably give CW 2 to 3K to release their lien. Whetehr CW will accept that or want more will be determined in large part to whether he has recourse loans or not.
Where is the property located? Are his loans original or refied? Thats a key question and will determine how successful he’ll be.