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I am almost ashamed to be in the same monastery as you, brother deprecated. :)
I just made a couple trips to the garage to carry down books I don't use anymore -- most of them technical, but very few of them Perl (I use the Perl ones). They could be put to better use, and you have mentioned a great use for them.
I have an idea to help you get this started: wishlists! You can make a wishlist for your young friends, or let them make their own on your recommendations. I have used craig's list to directly purchase art supplies for the schools in the SF Bay Area that don't see any of the Silicon Valley fortune. The hard part is getting people to remember to do it.
I waver on the point about investing in a charity fund. I find it hard to refute the point that I could better invest the money myself and use the proceeds directly (which I do). However, that argument has been twisted around for various reasons, and I will not get into the politics of tax evasion.
I applaud your idea and would be delighted to contribute (despite being jobless) in whatever way I can. Email me if you would like to know the titles of a few of the tech books I'd be willing to send out to interested parties.
In reply to Re: Diffusing Knowledge and Fortune to the Less Wise and Less Fortunate Monks.