Should I be concerned since he hasn’t worked in so long? ?

I am considering being in a relationship with someone I love deeply who has been my best friend through thick and thin for two years- but I am concerned about our future due to his lack of focus on work. He has a track record of achievement in the military, playing a sport in college, etc. but hasn’t consistently worked in two years. He was injured on duty and went through a divorce and really hard time 2.5 years ago (we met not long after his separation). He earns an income due to being injured in war, so his bills are covered and he has been in school. He now wants me to relocate to him, but I’m having concerns. Yes he’s in school, but he’s been majorly slacking and is lacking in direction. He could easily work in law enforcement & I keep suggesting he take a break from school - especially because he wants us to have a child and buy a home etc. so this would be a way to save. He goes back and forth though. He’ll say he may work and quit school, then say he doesn’t want more trauma related work- yet won’t commit to anything work wise. My concern is yes, he’s shown he has discipline through his past choices - but what if he’s become lazy and complacent due to a set monthly income? It seems like he got burnt out but thinks that he “could” be disciplined again just because he used to be. Should I give him time, or should this be a huge sign that he may not actually step it up? I don’t want to pressure him because he’s accepted & supported me through all- thoughts?