No. But I've thought that an underground, electronic lottery would be really sweet for the liberty movement.
I wonder if technology similar to bit-coin could facilitate this?
Yes. There already are underground bitcoin lotteries and betting games. There are not many people who are participating in them yet, but they are there. The largest jackpot I've seen was several hundred bitcoins, which is on the order of thousands of dollars. Small, but then your chances of winning are also a lot higher.