Would be great if you could arrange a yearly trip for anyone interested. Maybe you could list on the site who is attending so that if someone is interested in someone they might decide to attend to be able to meet the person face to face. Probably a good way to find a match because you can meet face to face and get to know each other in a social setting. Maybe a cruise or a sunny destination.
Money is the issue with that idea, at least if you want to use the vacation to meet people. This website has three real categories;
1) Too poor to pay for a vacation.
2) Wealthy enough to pay for a nice vacation
3) Wealthy enough to pay for a luxury vacation.
The thing is, most of the people are looking to date outside of their category.
Maybe if they made two different vacation plans right next to each other, one "Luxury", one "Nice", and also agreed to have the really wealthy people pay a percentage extra to let a truly poor person attend. But then you have to choose the poor people. Maybe make it a gender based lottery and the poor people have to buy a ticket for $100 to enter. Have the lottery gender balanced so that the number of total men equal the number of total women.
While the accomadations would be dramatically different, we could hold multiple cross-plan events where the really wealthy people can meet the others, at say a beach party and a night club, every day.