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This is a great idea. I've thought about this myself for years, but have never done anything about it being busy with personal career. This is just brainstorming, but in terms of splitting the risk among different investors, I wonder if you've looked at Lender's Club. They have a great model for small loans to random people. 
On the flip side of the spectrum, I wonder if there is some sort of a VC model that could be used here. VCs invest in 100 ideas with the goal that 9 out of 100 ideas pay them back 90 (startups go bankrupt) and 1 out of 100 ideas becomes the golden goose (like google). Applying this to education, what if you could get the person who is getting an education to commit to paying back 10x if they become a multi-millionaire? Not sure if there is something here, but maybe just something to think about.