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@Velocio
There are UK laws and regulation about such a thing.
http://www.institute-of-fundraising.org.uk/guidance/about-fundraising/raffles-and-lotteries/
If the raffle passes the criteria set down by those regulations, then I'd allow it. But, very few raffles do meet those criteria. It's a lot easier when the proceeds are going (in majority) to a cause or charity, and that there is transparency over the distribution of the funds and there can be some assurance and verification that the draw is random and fair.
We have done raffles on LFGSS, usually raising money for causes like the London Courier Emergency Fund (LCEF).
We have not permitted raffles for the sale of items whereby the proceeds are intended for a person rather than a cause or charity.
IF (and it's a big if), all of the criteria is met and I can be shown some documentation from the relevant local authorities that the raffle that raises funds for a private individual is OK. Then it will be permitted.
It should be noted that PayPal block raffles and fundraisers on the same ground and will freeze the account(s) that receive any money raised if they detect it.
It's a very highly regulated thing to prevent fraud, money laundering and restrict the activity confidence tricksters. I'm sure none of that applies here, but the simple fact is that I cannot allow raffles without being somewhat sure that it passes the regulation.