Only you can answer your financial questions. If you are moving and are going to be job hunting away from where you are now, then selling the leave makes some sense as traveling back and forth on permissive to house and job hunt would be expensive. IF you are currently using your GI bill you will need to work out with the VA once you have a dd214 in hand to get the stipend etc. Also do not overlook the usefullness of VA voc rehab. all the benefits of the gi bill PLUS job search help/placement and potential internships paid tax free on top of the housing stipend. Either way your last DoD pay check may be held for up to 2-3 months so put cash aside quick for that. (we have put aside as a family of 5 3 months worth of "full pay" and also 3-4 more months in zero balance credit card if need) Although I am all ready at the first denial stage of SSDI, and feel confident I will get it before its all over I make plans upon plans. GOod luck and congrats.