Should I confront my friend about his poor choices?

I'll start by saying I love this guy a lot, and that we have been friends for quite some time. Unfortunately, he keeps making incredibly irresponsible decisions, and it hurts me so much to see him (and his family) suffer as a result that I almost just don't want to see him again. Every time, he complains about how hard things are, but all of that hardship is a result of his own actions

The big things"

-Spent about four months on a drug/alcohol binge. During that time, became so broke that he couldn't afford condoms (but could afford MDMDA, weed, alcohol, coke, etc). He and his girlfriend are now raising a 9-month-old boy.

-Broke, on welfare, used the last of his savings to buy a very expensive engagement ring for his girlfriend, who he knows cheats on him and who refuses to try to find work.

-So broke now that they are basically starving (he's lost about 35 pounds in 4 months), he decided to borrow money from a "friend" (dealer) to buy a $7000 car.

So again, I really care about him (and his family), but every time I see him I spend three hours listening to how hard his life is. That's all we do anymore, is talk about how things suck. But because he's creating these situations himself, it really just makes me angry. Its hard to see somebody I care about hurt so bad. Is it worth talking to him? How?