To Re-enlist or not?

My husband has been in the service his whole life. He hasn't advanced in rank for 8 years but he asked me tonight if I thought he should re enlist or not. A few months ago he kept stressing about the future and the uncertainty of the job market, fearing the civilian world. I don't really know how to answer him. The military has given us some amazing opportunities but we also have dealt with a lot of stress with it as well (as I'm sure most of you have too and can relate). What kinds of things should I consider when discussing it with him? This year will be our five year anniversary so I haven't been a milspouse as long as he's been in. I'd like to eventually settle but I'm also worried about the job market too. Anyone have advice?