Hotels play a gamble game -- is a bigger event going to come in and sell out our rooms? If they think so, they will not give you a good deal.
If you make your contract years out (as I've heard Usenix does) you really play this game. In 2016, the Republican convention is planning to be in MythicalCity, as well as the Giant science fiction convention and the local college sports teams have been unbeatable the last few years, and that's likely to be a game weekend. It's now 2012, Does the hotel contract out half their space to one group and be an over-flow hotel for others, or do they gamble that they'll be the main hotel for one of those big events? When the smaller events come in, the ones that don't announce where they'll be until the year before, they're in a better position to deal. It's now 2015, The Republicans moved to OtherCity, GiantSFCon changed their mind and moved to another time of year, and the local sports teams are in a slump. OOoh, look, every hotel wants our business! And even events that plan only one year out can get bit. I help organize a 1000+ attendee technical conference (that's not part of Usenix). We approached two hotels two years ago to be our "conference hotel" at a specific rate. One made a bid, the other told us that they were sure another conference was going to fill them up and offered us some rooms at full price. Sucks to be them - The other conference fell through, and we wound up using the 2nd hotel as one of our overflow hotels, at our requested rate. When it comes to large scale planning, it's not like going on vacation. It's a whole other game.
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