I've never had a date raffle, but I did go on a "date" with a supportive member during my time at the Las Vegas AVNs, as a way to show my appreciation. My experience is of course a little different than a date raffle as I got to "pick" my date, but I feel it's a valuable experience nonetheless. We went out for dinner at a hotel and all in all had a pleasant time. Yes, it was a little bit awkward and weird, but only because we were two people who are more so shy and timid and didn't know how to keep the conversation rolling. We tried to find some common ground but in the end we only really had MFC in common, so the conversation was mostly about that. He was a gentleman and wasn't trying to touch my boobs or something and never once talked about anything sexual.
In the end we hung out during most of my time in Vegas. He was a very nice, timid guy, sometimes a little awkward in his nerdy way, but never made me uncomfortable. My mind frame about meeting members is: they are there in your room (almost) every day, tipping or supporting you with chat. Going to the AVNs was my way of reaching out (as a human being, not a model) to the members to say "thank you" for being there. Some girls may think, "yeah but this is my job and I'm just here for a pay check", but in my mind, in any job you go the extra distance and make friends with coworkers and clients, because we are human and we thrive on connection. Did I get direct monetary payment for the date? No, but he paid me back in so many other ways. He became an incredibly loyal (tipping) member, paid for dinner, bought me a dress I was coveting as a way of saying thank you, and bought me a ticket to the cam girl after party in order to include me in on the fun.
Honestly, I hear a lot of horror stories too, but I hear them from members. There seems to be a lot of negativity surrounding the models, as a lot of them just don't seem to treat the members as human beings. They explicitly act uncomfortable as if the member is there to violate them, they clearly don't show any interest and are always on their phone. They bring another model for "protection" (which I agree is a good idea) but then completely ignore the member... the list goes on and on. A lot of models don't seem to give the members a chance. But this is just what I've heard from people on the receiving end of date raffles. It's just a recipe for disaster.
I think the key to making a successful date raffle is an open mind and a caring personality. OF COURSE there are weird people on MFC and you have to be careful. Date raffles aren't always going to be positive because you might fall on one of those really weird ones. But if you go the extra distance and try to have an honest human interaction, I think the experience can be really rewarding.