I've gone to Wilson demos, I consider it a fun experience to get a taste of different goals. It's pretty enjoyable usually, some wine and snacks laid out, poking around before and after to look at the fit/finish, which is first rate. I further enjoy contrasting my listening experience with what I know are questionable measurements. To me it simply means, whether through perception or incomplete science, there may be a little more to it than some on axis measurements. Don't get me wrong, I personally purchase speakers that speak to me AND measure competently, but if Brand X measures poorly yet stirs the soul of someone else, who am I to judge? I mean, I'll stick to my Revels but I do have an interest in speakers of all types. Can't seem to stop loving them.
The last Wilson demo I went to they had a decent setup and were using room correction, so the sound was a combo of the equipment and the target curve, which was not disclosed, chosen by the staff. I can tell you there was a lot of fiddling around with settings by one guy while the other talked a bit before starting the next track, so it was my suspicion they used track-by-track eq, dialed in by the staff, but this is just a guess.
As to why they were speaker of the year? Who knows. I don't really pay too much attention to that stuff, fun to read and experience but relies too heavily on the unknown things, at the expense of the known things, at a cost that I can't afford, for me to get serious about saving up for a purchase of that magnitude.