I called on my NYC expert, also known as Dora from My Preconceived Notion, and discussed possible locations. Dora said that finding a good location for a group our size (around 20) can be problematic in that area of NYC. And, since we are trying to keep it indoors since the weather could mess up an outdoor get together, we concluded that the hotel lobby and coffee/juice/etc would be the best option. As a rule, hotels are willing to hold onto luggage for a bit if there is a gap between your check out time and departure time. That means we wouldn't have to worry about our luggage while we enjoy each others company.
The only remaining questions are what time do we plan this for and how do you feel about children at the get together. I know many of you still haven't had the child you long for and the presence of little ones can be painful. I also know that a few of the people integral to this community will not be able to be there if kids are not welcome.
So, to sum it up:
Location: lobby of the Hilton (we can always move it outside if the weather is good)
Time: post check out (mention a time in the comments if you have a specific time in mind)
Kids or no kids: answer the poll below