1. Now is not the time to open ANY show on Broadway. Over a dozen shows have either closed or as closing this weekend, primarily due to the economy but also because January through March is traditionally a dead time on Broadway anyway. A couple (like that planned revival of "Hair" with Diana DeGarmo) closed before even going to previews because too many backers pulled out. The holiday tourists have left and the deep freeze takes over. The only shows still running at this point are the long-running hits ("Phantom," "Chicago," etc.) and a few of the new favorites. With the economy of NYC so intrinsically tied to Wall Street and financiers, it is going to get worse before it gets better.
2. The reason why "Annie" closed on Broadway in 1983 was because between the various road companies and the movie, it was no longer necessary for families to spend the money to go see the Broadway production. That is still true today. This production has been touring for years now and without that, it is one of the top few shows produced by community theatres because it's popular and allows a lot of kids to be involved. If I am being completely honest, I think "Annie" on Broadway would be a disaster right now because it is already overexposed around the country. The best way to launch a revival is to make the public miss the material and then usher it in again. That is one of the reasons why "South Pacific" has been doing so well. It hasn't been on Broadway since the original run in the '40s, the movie was made decades and decades ago and the majority of the more modern shows, for better or worse, sound very far removed than that rich Rodgers and Hammerstein score.