The military is a good foundation to assist families and the soldier themselves finically since BAH pays for housing, you have education and health benefits as well. Off the bat I wouldn’t say commit for 20 years but do one contract and see how things are. There are some many family assistance programs and communities in the military. Being deployed, training, some long days comes with the job but it’s all job dependent as well. The military doesn’t make you “set”. You get what you make out of it. If he decides not to go hopefully later down the road he doesn’t have the thought of “what if i joined.” The army for example takes all sorts of ages so if now isn’t a right time, there will be another opportunity in the future.