Player really can't afford to play

[pfapfap]

I think scott's answer is a good way to prevent him from getting destroyed when he's left with good players. Let him at least end on the good side of luck. Also, yeah, dumping some chips to him from time to time isn't a bad idea either. These are microstakes.

If he enjoys playing, then help him out. Turn this into a poker study group. At showdowns, talk about how you played your hand and why. When you react to his play, tell him your reads and why they're your reads. Throw out some poker proverbs when appropriate (eg, when folding TPTK against a big raise, say "don't go broke with one pair"), etc. These are your buddies and the stakes are tiny. This isn't tapping the glass, it's helping out friends so that you can all enjoy this activity together.