You could go with a medium sized city. Manchester, NH for example has a couple fairly good sized conference centers, is usually cheaper to fly to than boston, has free parking, a good "strip" with plenty of good restaraunts.
It's not a big city, but you're not in the middle of nowhere either.
The major problem with holding the conference in other cities than New York is that the bulk of the organizers live in....New York! We're all volunteers and it's difficult enough to take a couple days of work to prepare for a conference taking place "in our backyard" so to speak. It would be another beast entirely to try and plan and execute everything remotely.
Another issue is that holding the conference in a more "out of the way" location means our speaker expenses may rise considerably. Right now we can take advantage of NY or northeast-based speakers without paying much in travel expenses. Holding the conference in a place that does not have a built-in speaker base or is not a major transportation hub changes things.
So, as always, it's a tough line to walk....
