Player really can't afford to play

[Dromar]

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so I ended up getting him HoH volume 1 for his birthday.

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I like this idea. It's a subtle hint, yet not insulting in any way. It's always difficult to talk to a friend about how bad they play (obviously) because you don't want to insult their intelligence. Buying him a book as a gift literally puts his problem into his own hands. As other people have said, he's an adult capable of making his own decisions. If you give him the chance to learn and get better, there's no excuse, and IMO nothing more that you can (or should) do.

I'm in a somewhat similar situation as described in the OP, but much less intense. I have a friend (actually, one of my best friends) who is pretty bad at poker. We play $.1/.25 NLHE cash game at his request and insistence. We had played LHE and/or limit dealer's choice in the past, but now he insists on playing NLHE. Fortunately, I haven't had to take action because:
1. He's got a job
2. He has nobody to support
3. He will occasionally win (like one time in 10 he'll be up $30)
4. He usually stops buying in after $60 or $80.
5. A couple of the other players in the game aren't much better than he is (though they tend not to lose as much on average).



To OP: I think you're doing the right thing by taking action, but you need to be careful to neither insult his intelligence nor make decisions for him. He is an adult, and in the end it's solely his responsibility and his decision to manage his money. It's too bad that he keeps rebuying. He must rebuy 6 or 7 times to get $150 in the hole. Maybe you could play shorter sessions to limit his potential loss. I think stopping the game when it gets to the point of having >4 people is a good idea. When it gets down to you, GoodP, and LAGP, it's one person losing a bunch of money, and two people feeling guilty about it. What fun is that?