He violated one of the first rules of responsible personal finance: live under your means, because someday your means may suddenly change. That is easier said than done as a young man, but this dude had a 30 year career as an officer, then six years making 150k as a contractor, yet 2 years after that he suddenly is homeless because he can't pay his bills when he's bringing in almost 4k per month tax free.
He needs to wise up. Stop paying the kids tuition, stop paying for his wife to live in a house he can't even if that means sucking up a divorce, stop saying he's mulling over what job is right for him when he should take anything he can get, etc.
If this guy has to be homeless he likely doesn't have many assets, how much could a divorce impact him if she has no claim to his disability. He's just being stupid.